Insecticides

ABSTRACT

Compounds of formula I 
                         
wherein the substituents are as defined in claim  1 , and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I can be used as agrochemical active ingredients and can be prepared in a manner known per se.

This application is a 371 of International Application No.PCT/EP2005/010891 filed Oct. 10, 2005, which claims priority to GB0422556.1 filed Oct. 11, 2004, the contents of which are incorporatedherein by reference.

The present invention relates to novel anthranilamide derivatives, toprocesses for their preparation, to compositions comprising thosecompounds, and to their use for controlling insects or representativesof the order Acarina.

Anthranilamide derivatives with insecticidal properties are known anddescribed, for example, in WO 01/70671, WO 03/016284, WO 03/015518, WO03/024222 and WO 04/033468. There have now been found novelanthranilamide derivatives with pesticidal properties, especially forthe control of insects and members of the order Acarina.

The present invention accordingly relates to compounds of formula I

wherein

-   each of E and Z, which may be the same or different, represents    oxygen or sulfur;-   A is C₁-C₆alkylene, C₂-C₆alkenylene, C₂-C₆alkynylene, or a bivalent    three- to ten-membered monocyclic or fused bicyclic ring system    which can be partially saturated or fully saturated and can contain    1 to 4 hetero atoms selected from the group consisting of nitrogen,    oxygen and sulfur, it not being possible for each ring system to    contain more than 2 oxygen atoms and more than 2 sulfur atoms;-   and it being possible for the three- to ten-membered ring system    itself and also for the C₁-C₆alkylene, C₂-C₆alkenylene and    C₂-C₆alkynylene groups to be mono-, di- or trisubstituted by    halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl,    C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl,    C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,    C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl,    C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,    C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino,    C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,    C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,    C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or    C₃-C₆-trialkylsilyl, or by-   a three- to ten-membered monocyclic or fused bicyclic ring system    which can be aromatic, partially saturated or fully saturated and    can contain 1 to 4 hetero atoms selected from the group consisting    of nitrogen, oxygen and sulfur, it not being possible for each ring    system to contain more than 2 oxygen atoms and more than 2 sulfur    atoms, and it being possible for the three- to ten-membered ring    system itself to be mono-, di- or trisubstituted by halogen, cyano,    nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,    C₃-C₆cycloalkyl, C₅-C₇Cycloalkenyl, C₅-C₈cycloalkynyl,    C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,    C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl,    C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,    C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino,    C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,    C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,    C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy,    C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl    group in turn to be substituted by hydroxy, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio,    C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio,    C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio,    C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio, cyano-C₁-C₃alkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,    C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl,    N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano    or nitro; and substituents at nitrogen atoms in the ring systems    being other than halogen;-   X is oxygen, NH or C₁-C₄alkyl-N;-   Y is C₁-C₆alkylene, C₂-C₆alkenylene, C₂-C₆alkynylene, or a bivalent    three- to ten-membered monocyclic or fused bicyclic ring system    which can be partially saturated or fully saturated and can contain    1 to 4 hetero atoms selected from the group consisting of nitrogen,    oxygen and sulfur, it not being possible for each ring system to    contain more than 2 oxygen atoms and more than 2 sulfur atoms;-   and it being possible for the three- to ten-membered ring system    itself and also for the C₁-C₆alkylene, C₂-C₆alkenylene and    C₂-C₆alkynylene groups to be mono-, di- or trisubstituted by    halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl,    C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl,    C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,    C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl,    C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,    C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino,    C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,    C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,    C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or    C₃-C₆-trialkylsilyl, or by a three- to ten-membered monocyclic or    fused bicyclic ring system which can be aromatic, partially    saturated or fully saturated and can contain 1 to 4 hetero atoms    selected from the group consisting of nitrogen, oxygen and sulfur,    it not being possible for each ring system to contain more than 2    oxygen atoms and more than 2 sulfur atoms, and it being possible for    the three- to ten-membered ring system itself to be mono-, di- or    trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl,    C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl,    C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl,    C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl,    C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio,    C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,    C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,    C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,    C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy,    C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl    group in turn to be substituted by hydroxy, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio,    C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio,    C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio,    C₂-C₄alkoxycarbonyl-C₁-C₃-alkylthio, cyano-C₁-C₃alkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,    C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl,    N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano    or nitro; and substituents at nitrogen atoms in the ring systems    being other than halogen;-   p is 0 or 1;-   q is 0 or 1;-   B is a three- to four-membered ring system which is fully or    partially saturated and can contain a hetero atom selected from the    group consisting of nitrogen, oxygen and sulfur, and it being    possible for the three- to four-membered ring system itself to be    mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy,    C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl,    C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl,    C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl,    C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy,    C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,    C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino,    C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,    C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,    C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy,    C₃-C₆-trialkylsilyl, or by a three- to ten-membered monocyclic or    fused bicyclic ring system which can be aromatic, partially    saturated or fully saturated and can contain 1 to 4 hetero atoms    selected from the group consisting of nitrogen, oxygen and sulfur,    it not being possible for each ring system to contain more than 2    oxygen atoms and more than 2 sulfur atoms, and it being possible for    the three- to ten-membered ring system itself to be mono-, di- or    trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl,    C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl,    C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl,    C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl,    C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio,    C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,    C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,    C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,    C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy,    C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl    group in turn to be substituted by hydroxy, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio,    C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio,    C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio,    C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio, cyano-C₁-C₃alkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,    C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl,    N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano    or nitro; and substituents at nitrogen atoms in the ring systems    being other than halogen;-   each R₁ independently is halogen, nitro, hydroxy, C₁-C₆alkyl,    C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,    C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl,    C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,    C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylsulfinyl,    C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino,    C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino,    C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or    C₃-C₆-trialkylsilyl, phenyl, benzyl or phenoxy, or phenyl, benzyl or    phenoxy mono-, di- or trisubstituted by halogen, cyano, nitro,    halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl,    C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,    C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio,    C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,    C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,    C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,    C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or    C₃-C₆-trialkylsilyl;-   or each R₁ independently is amino, formyl, C₂-C₆cyanoalkenyl,    C₂-C₆alkylcarbonylamino, phenylcarbonylamino which can be mono-, di-    or trisubstituted by halogen, cyano, nitro, halogen, C₁-C₆alkyl,    C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,    C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl,    C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,    C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino,    C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,    C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,    C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or    C₃-C₆trialkylsilyl; or each R₁ independently is 2-,3- or    4-pyridylcarbonylamino which can be mono-, di- or trisubstituted by    halogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl,    C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl,    C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,    C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl,    C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino,    C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino,    C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or    C₃-C₆-trialkylsilyl; or each R₁ independently is    C₂-C₆alkoxycarbonylamino, C₂-C₆alkylaminocarbonylamino,    C₃-C₆dialkylaminocarbonylamino, C₂-C₆haloalkylcarbonyl or is a group    R_(x)ON═C(R_(y))—, wherein R_(x) and R_(y) independently are    hydrogen or C₁-C₆alkyl;-   n is 0, 1, 2, 3 or 4;-   each of R₂ and R₃, which may be the same or different, represents    hydrogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl or C₃-C₈cycloalkyl;    or C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl or C₃-C₈cycloalkyl    substituted by one or more substituents selected from halogen nitro,    cyano, hydroxy, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio,    C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,    C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino and    C₁-C₆alkyl-C₃-C₆cycloalkylamino;-   D is phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl; or phenyl,    2-pyridyl, 3-pyridyl or 4-pyridyl mono-, di- or trisubstituted by    C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, halogen, cyano,    C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,    C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl or    C₁-C₄haloalkylsulfonyl; or D is a group

-   R₄, R₄′, R₁₀, R₁₇, and R₁₉ independently from each other, are    hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, halogen,    cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₄alkoxycarbonyl,    C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl,    C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl or    C₁-C₄haloalkylsulfonyl;-   R₅, R₆, R₈, R₁₁, R₁₂, R₁₅, R₁₆ and R₁₈ independently from each    other, are C₁-C₆alkyl or C₁-C₆alkyl mono-, di- or trisubstituted by    halogen, cyano, nitro, hydroxy, C₁-C₄alkoxy, C₂-C₄alkoxycarbonyl,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,    C₁-C₄alkylamino, C₂-C₄dialkylamino or C₃-C₆cycloalkylamino; or are    phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl; or are phenyl, 2-pyridyl,    3-pyridyl or 4-pyridyl mono-, di- or trisubstituted by C₁-C₆alkyl,    C₃-C₆cycloalkyl, C₁-C₆haloalkyl, halogen, cyano, C₁-C₄alkoxy,    C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,    C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl or    C₁-C₄haloalkylsulfonyl;-   R₇, R₉, R₁₃ and R₁₄ independently from each other, are hydrogen,    C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,    C₃-C₆alkenyl or C₃-C₆haloalkenyl and agronomically acceptable    salts/isomers/enantiomers/tautomers/N-oxides of those compounds,    with the exception of the compound    2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic    acid [2-methyl-6-(oxiranylmethyl-carbamoyl)-phenyl]-amide.

Compounds I which have at least one basic centre can form, for example,acid addition salts, for example with strong inorganic acids such asmineral acids, for example perchloric acid, sulfuric acid, nitric acid,nitrose acid, a phosphorus acid or a hydrohalic acid, with strongorganic carboxylic acids, such as C₁-C₄alkanecarboxylic acids which areunsubstituted or substituted, for example by halogen, for example aceticacid, such as saturated or unsaturated dicarboxylic acids, for exampleoxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid orphthalic acid, such as hydroxycarboxylic acids, for example ascorbicacid, lactic acid, malic acid, tartaric acid or citric acid, or such asbenzoic acid, or with organic sulfonic acids, such as C₁-C₄alkane- orarylsulfonic acids which are unsubstituted or substituted, for exampleby halogen, for example methane- or p-toluenesulfonic acid. Compounds Iwhich have at least one acidic group can form, for example, salts withbases, for example mineral salts such as alkali metal or alkaline earthmetal salts, for example sodium, potassium or magnesium salts, or saltswith ammonia or an organic amine, such as morpholine, piperidine,pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-,diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- ortrihydroxy-lower-alkylamine, for example mono-, di- or triethanolamine.Where appropriate, the corresponding internal salts can furthermore beformed. Preferred within the scope of the invention are agrochemicallyadvantageous salts; however, the invention also encompasses salts whichhave disadvantage for agrochemical use, for example salts which aretoxic to bees or fish, and which are employed, for example, for theisolation or purification of free compounds I or agrochemicallyutilizable salts thereof. Owing to the close relationship between thecompounds I in free form and in the form of their salts, for thepurposes of the invention the free compounds I or their saltshereinabove and hereinbelow are respectively to be understood asincluding, where appropriate, the corresponding salts or the freecompounds I. The same applies analogously to tautomers of compounds Iand salts thereof. In general, the free form is preferred in each case.

The alkyl groups occurring in the definitions of the substituents can bestraight-chain or branched and are, for example, methyl, ethyl,n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl,hexyl, heptyl and octyl and their branched isomers. Alkoxy, alkenyl andalkynyl radicals are derived from the alkyl radicals mentioned. Thealkenyl and alkynyl groups can be mono- or polyunsaturated.

Halogen is generally fluorine, chlorine, bromine or iodine. This alsoapplies, correspondingly, to halogen in combination with other meanings,such as haloalkyl or halophenyl.

Haloalkyl groups preferably have a chain length of from 1 to 6 carbonatoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl,1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl,difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

Suitable haloalkenyl groups are alkenyl groups which are mono- orpolysubstituted by halogen, halogen being fluorine, chlorine, bromineand iodine and in particular fluorine and chlorine, for example2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl,3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl and4,4,4-trifluorobut-2-en-1-yl. Among the C₃-C₂₀alkenyl groups which aremono-, di- or trisubstituted by halogen, preference is given to thosehaving a chain length of from 3 to 5 carbon atoms.

Suitable haloalkynyl groups are, for example, alkynyl groups which aremono- or polysubstituted by halogen, halogen being bromine, iodine andin particular fluorine and chlorine, for example 3-fluoropropynyl,3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and4,4,4-trifluorobut-2-yn-1-yl. Among the alkynyl groups which are mono-or polysubstituted by halogen, preference is given to those having achain length of from 3 to 5 carbon atoms.

Alkoxy groups preferably have a preferred chain length of from 1 to 6carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy,i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy and also theisomeric pentyloxy and hexyloxy radicals; preferably methoxy and ethoxy.

Alkoxycarbonyl is, for example, methoxycarbonyl (C₂-alkoxycarbonyl),ethoxycarbonyl (C₃-alkoxycarbonyl), propoxycarbonyl, isopropoxycarbonyl,n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl ortert-butoxycarbonyl; preferably methoxycarbonyl or ethoxycarbonyl.Haloalkoxy groups preferably have a chain length of from 1 to 6 carbonatoms. Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy,trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy,2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy andtrifluoromethoxy. Alkylthio groups preferably have a chain length offrom 1 to 6 carbon atoms. Alkylthio is, for example, methylthio,ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio,sec-butylthio or tert-butylthio, preferably methylthio and ethylthio.Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl,propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl,sec-butylsulfinyl, tert-butylsulfinyl; preferably methylsulfinyl andethylsulfinyl.

Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl,propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl,sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl orethylsulfonyl. Alkoxyalkoxy groups preferably have a chain length offrom 1 to 8 carbon atoms. Examples of alkoxyalkoxy groups are:methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy,ethoxyethoxy, propoxymethoxy or butoxybutoxy. Alkylamino is, forexample, methylamino, ethylamino, n-propylamino, isopropylamino or theisomeric butylamines. Dialkylamino is, for example, dimethylamino,methylethylamino, diethylamino, n-propylmethylamino, dibutylamino anddiisopropylamino. Preference is given to alkylamino groups having achain length of from 1 to 4 carbon atoms. Alkylaminocarbonyl is, forexample, methylaminocarbonyl (C₂-alkylaminocarbonyl) orethylaminocarbonyl (C₃-aminocarbonyl). Alkoxyalkyl groups preferablyhave a chain length of 1 to 6 carbon atoms. Alkoxyalkyl is, for example,methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl,n-propoxyethyl, isopropoxymethyl or isopropoxyethyl. Alkylthioalkylgroups preferably have from 1 to 8 carbon atoms. Alkylthioalkyl is, forexample, methylthiomethyl, methylthioethyl, ethylthiomethyl,ethylthioethyl, n-propylthiomethyl, n-propylthioethyl,isopropylthiomethyl, isopropylthioethyl, butylthiomethyl, butylthioethylor butylthiobutyl. The cycloalkyl groups preferably have from 3 to 6ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl. Phenyl, also as part of a substituent such as phenoxy,benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl, phenoxyalkyl, maybe substituted. In this case, the substituents can be in ortho, metaand/or para position. The preferred substituent positions are the orthoand para positions to the ring attachment point.

Examples for B as a optionally substituted three- to four-membered ringsystem which is fully or partially saturated and can contain a heteroatom selected from the group consisting of nitrogen, oxygen and sulfur,are cyclopropyl, methyl-cyclopropyl, cyclopropenyl, cyclobutyl,cyclobutenyl,

According to the present invention, a three- to ten-membered, monocyclicor fused bicyclic ring system which may be partially saturated or fullysaturated is, depending of the number of ring members, for example,selected from the group consisting of

cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, where said cycloalkylgroups for their part may be preferably unsubstituted or substituted byC₁-C₆alkyl or halogen, or is

wherein each R₂₆ is methyl, each R₂₇ and each R₂₈ are independentlyhydrogen, C₁-C₃alkyl, C₁-C₃alkoxy, C₁-C₃alkylthio or trifluoromethyl, X₄is oxygen or sulfur and r=1, 2, 3 or 4.

Where no free valency is indicated in those definitions, for example asin

the linkage site is located at the carbon atom labelled “CH” or in acase such as, for example,

at the bonding site indicated at the bottom left. The second valence forthe bivalent ring system of substituent A or Y can be located at anysuitable position of the ring.

According to the present invention, a three- to ten-membered monocyclicor fused bicyclic ring system which may be aromatic, partially saturatedor fully saturated is, depending of the number of ring members, forexample, selected from the group consisting of

cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, where said cycloalkylgroups for their part may be preferably unsubstituted or substituted byC₁-C₆alkyl or halogen, or is phenyl, benzyl, naphthyl or the followingheterocyclic groups: pyrrolyl; pyridyl; pyrazolyl; pyrimidyl; pyrazinyl;imidazolyl; thiadiazolyl; quinazolinyl; furyl; oxadiazolyl; indolizinyl;pyranyl; isobenzofuranyl; thienyl; naphthyridinyl;(1-methyl-1H-pyrazol-3-yl)-; (1-ethyl-1H-pyrazol-3-yl)-;(1-propyl-1H-pyrazol-3-yl)-; (1H-pyrazol-3-yl)-;(1,5-dimethyl-1H-pyrazol-3-yl)-; (4-chloro-1-methyl-1H-pyrazol-3-yl)-;(1H-pyrazol-1-yl)-; (3-methyl-1H-pyrazol-1-yl)-;(3,5-dimethyl-1H-pyrazol-1-yl)-; (3-isoxazolyl)-;(5-methyl-3-isoxazolyl)-; (3-methyl-5-isoxazolyl)-; (5-isoxazolyl)-;(1H-pyrrol-2-yl)-; (1-methyl-1H-pyrrol-2-yl)-; (1H-pyrrol-1-yl)-;(1-methyl-1H-pyrrol-3-yl)-; (2-furanyl)-; (5-methyl-2-furanyl)-;(3-furanyl)-; (5-methyl-2-thienyl)-; (2-thienyl)-; (3-thienyl)-;(1-methyl-1H-imidazol-2-yl)-; (1H-imidazol-2-yl)-;(1-methyl-1H-imidazol-4-yl)-; (1-methyl-1H-imidazol-5-yl)-;(4-methyl-2-oxazolyl)-; (5-methyl-2-oxazolyl)-; (2-oxazolyl)-;(2-methyl-5-oxazolyl)-; (2-methyl-4-oxazolyl)-; (4-methyl-2-thiazolyl)-;(5-methyl-2-thiazolyl)-; (2-thiazolyl)-; (2-methyl-5-thiazolyl)-;(2-methyl-4-thiazolyl)-; (3-methyl-4-isothiazolyl)-;(3-methyl-5-isothiazolyl)-; (5-methyl-3-isothiazolyl)-;(1-methyl-1H-1,2,3-triazol-4-yl)-; (2-methyl-2H-1,2,3-triazol-4-yl)-;(4-methyl-2H-1,2,3-triazol-2-yl)-; (1-methyl-1H-1,2,4-triazol-3-yl)-;(1,5-dimethyl-1H-1,2,4-triazol-3-yl)-;(3-methyl-1H-1,2,4-triazol-1-yl)-; (5-methyl-1H-1,2,4-triazol-1-yl)-;(4,5-dimethyl-4H-1,2,4-triazol-3-yl)-;(4-methyl-4H-1,2,4-triazol-3-yl)-; (4H-1,2,4-triazol-4-yl)-;(5-methyl-1,2,3-oxadiazol-4-yl)-; (1,2,3-oxadiazol-4-yl)-;(3-methyl-1,2,4-oxadiazol-5-yl)-; (5-methyl-1,2,4-oxadiazol-3-yl)-;(4-methyl-3-furazanyl)-; (3-furazanyl)-;(5-methyl-1,2,4-oxadiazol-2-yl)-; (5-methyl-1,2,3-thiadiazol-4-yl)-;(1,2,3-thiadiazol-4-yl)-; (3-methyl-1,2,4-thiadiazol-5-yl)-;(5-methyl-1,2,4-thiadiazol-3-yl)-; (4-methyl-1,2,5-thiadiazol-3-yl)-;(5-methyl-1,3,4-thiadiazol-2-yl)-; (1-methyl-1H-tetrazol-5-yl)-;(1H-tetrazol-5-yl)-; (5-methyl-1H-tetrazol-1-yl)-;(2-methyl-2H-tetrazol-5-yl)-; (2-ethyl-2H-tetrazol-5-yl)-;(5-methyl-2H-tetrazol-2-yl)-; (2H-tetrazol-2-yl)-; (2-pyridyl)-;(6-methyl-2-pyridyl)-; (4-pyridyl)-; (3-pyridyl)-;(6-methyl-3-pyridazinyl)-; (5-methyl-3-pyridazinyl)-; (3-pyridazinyl)-;(4,6-dimethyl-2-pyrimidinyl)-; (4-methyl-2-pyrimidinyl)-;(2-pyrimidinyl)-; (2-methyl-4-pyrimidinyl)-; (2-chloro-4-pyrimidinyl)-;(2,6-dimethyl-4-pyrimidinyl)-; (4-pyrimidinyl)-;(2-methyl-5-pyrimidinyl)-; (6-methyl-2-pyrazinyl)-; (2-pyrazinyl)-;(4,6-dimethyl-1,3,5-triazin-2-yl)-; (4,6-dichloro-1,3,5-triazin-2-yl)-;(1,3,5-triazin-2-yl)-; (4-methyl-1,3,5-triazin-2-yl)-;(3-methyl-1,2,4-triazin-5-yl)-; (3-methyl-1,2,4-triazin-6-yl)-;

wherein each R₂₆ is methyl, each R₂₇ and each R₂₈ are independentlyhydrogen, C₁-C₃alkyl, C₁-C₃alkoxy, C₁-C₃alkylthio or trifluoromethyl, X₄is oxygen or sulfur and r=1, 2, 3 or 4.

Where no free valency is indicated in those definitions, for example asin

the linkage site is located at the carbon atom labelled “CH” or in acase such as, for example,

at the bonding site indicated at the bottom left.

Compounds of formula I are preferred, wherein R₄′ is hydrogen and eachR₁ independently is halogen, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl,C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl,C₁-C₄haloalkylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl,C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy,C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl, phenyl, benzyl orphenoxy, or phenyl, benzyl or phenoxy mono-, di- or trisubstituted byhalogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio,C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl,C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy,C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl.

In especially preferred compounds of formula I,

-   B is a three- to four-membered ring system which is fully or    partially saturated, and it being possible for the three- to    four-membered ring system itself to be mono-, di- or trisubstituted    by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl,    C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl,    C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,    C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl,    C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,    C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino,    C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,    C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,    C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy,    C₃-C₆-trialkylsilyl, or by a three- to ten-membered monocyclic or    fused bicyclic ring system which can be aromatic, partially    saturated or fully saturated and can contain 1 to 4 hetero atoms    selected from the group consisting of nitrogen, oxygen and sulfur,    it not being possible for each ring system to contain more than 2    oxygen atoms and more than 2 sulfur atoms, and it being possible for    the three- to ten-membered ring system itself to be mono-, di- or    trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl,    C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl,    C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl,    C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl,    C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio,    C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,    C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,    C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,    C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,    C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,    C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy,    C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl    group in turn to be substituted by hydroxy, C₁-C₆alkyl,    C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio,    C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio,    C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio,    C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio, cyano-C₁-C₃alkylthio,    C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,    C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl,    N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano    or nitro; and substituents at nitrogen atoms in the ring systems    being other than halogen.

Preference is given to subgroups of compounds of formula I wherein

-   a) p and/or q is 0;-   b) E and/or Z is oxygen; and/or-   c) R₂ and/or R₃ is hydrogen.-   X is preferably oxygen, NH; NMe or NEt.-   Y is preferably C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene    or, C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene substituted by    halogen, C₃-C₆cycloalkyl, C₁-C₄alkylsulfonyl or C₁-C₄alkoxy.

Special mention should be made of compounds of formula I wherein R₁ isselected from C₁-C₄alkyl, halogen, C₁-C₅haloalkyl, nitro, C₁-C₄alkoxy,C₁-C₄-haloalkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl andC₁-C₄haloalkylsulfonyl, in particular from halogen and C₁-C₆alkyl,preferably selected from methyl and halogen, most preferably selectedfrom methyl and chloro, and n is 1 or 2, preferably 2. Preferredposition of R₁ is meta to the group —C(Z)—N(R₃)-A-(X)p—(Y)q—B.

An outstanding group of compounds of formula I comprises those compoundswherein A is C₁-C₆alkylene which may be substituted by C₃-C₆cycloalkyl,C₂-C₆alkenyl, cyano, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkoxy,halogen or C₁-C₆haloalkyl; or A is C₃-C₆cycloalkylene. Preferably A isC₁-C₆alkylene or cyclopropylene, most preferably methylene orcyclopropylene.

In further preferred compounds of formula I, B is cyclopropyl orcyclobutyl, preferably cyclopropyl.

Special emphasis should also be given to compounds of formula I whereinD is a group D₁, wherein R₅ is 2-pyridyl which can be substituted byhalogen, preferably which is monosubstituted by chloro at the 3-positionof the pyridine ring, R₄′ is hydrogen or halogen, preferably hydrogenand R₄ is halogen preferably chloro and bromo, C₁-C₆haloalkyl preferablytrifluoromethyl, C₁-C₄haloalkoxy, preferably 2,2,2-trifluoroethoxy.

Preference is also given to compounds of formula I wherein B iscyclopropyl or cyclobutyl which may be mono- di-, or trisubstituted byhalogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio; or Bis CH(CH₂O), CH(CHMeO), CH—(CMe₂O), CH(CH₂S), CH(CH₂OCH₂), CH(CHMeOCH₂),CH(CMe₂OCH₂), CH(CH₂S—(O)₂CH₂), CH(CHMeS(O)₂CH₂), CH(CMe₂S(O)₂CH₂),C(Me)-(CH₂O), C(Me)(CHMeO), C(Me)-(CMe₂O), C(Me)-(CH₂S),C(Me)-(CH₂OCH₂), C(Me)(CHMeOCH₂), C(Me)-(CMe₂OCH₂), C(Me)-(CH₂S(O)₂CH₂),C(Me)-(CHMe-S(O)₂CH₂) or C(Me)-(CMe₂-S(O)₂CH₂). In especially preferredcompounds of formula I B is cyclopropyl or cyclobutyl which may besubstituted by halogen or methyl, in particular by chloro, bromo andmethyl; preferably B is cyclopropyl.

In an outstanding group of compounds of formula I the substituents havethe following meanings:

-   n is 2 and one R₁ is C₁-C₄alkyl, preferably methyl, or halogen,    preferably chloro, the other R₁ is halogen preferably chloro or    bromo; wherein most preferably one R₁ with the meaning C₁-C₄alkyl    occupies the ortho position with regard to the group —N(R₂)—C(E)-D.-   D is a group D₁, wherein R₄′ is hydrogen, R₄ is halogen preferably    chloro and bromo, C₁-C₆haloalkyl preferably trifluoromethyl,    C₁-C₄haloalkoxy, preferably 2,2,2-trifluoroethoxy and R₅ is    2-pyridyl monosubstituted by halogen, preferably by 3-chloro;-   R₂ and R₃ are hydrogen;-   A is C₁-C₆alkylene or a fully saturated bivalent 3- to 6-membered    monocyclic ring system, preferably methylene, cyclopropylene or    cyclobutylene, most preferably a fully saturated bivalent 3- to    6-membered monocyclic ring system, in particular cyclopropylene or    cyclobutylene;-   p and q are 0;-   E and Z are oxygen;-   and B is cyclopropyl or cyclobutyl, preferably cyclopropyl.

The process according to the invention for preparing compounds offormula I is carried out analogously to known processes, for examplethose described in WO 01/70671, WO 03/016284, WO 03/015518 and WO04/033468.

The process for the preparation of a compound of formula I or, whereappropriate, a tautomer thereof, in each case in free form or in saltform, comprises

-   a) for the preparation of a compound of formula I, in which R₂ is    hydrogen and E and Z are oxygen, or, where appropriate, a tautomer    and/or salt thereof,-   reacting a compound of formula II

-   in which R₁, n, and D have the meanings given for formula I in claim    1, or, where appropriate, a tautomer and/or salt thereof with a    compound of formula III    HN(R₃)-A-(X)_(p)—(Y)_(q)—B  (III),-   in which R₃, A, X, Y, p, q and B have the meanings given for formula    I, or, where appropriate, with a tautomer and/or salt thereof or,-   b) for the preparation of a compound of formula I, or, where    appropriate, a tautomer and/or salt thereof,-   reacting a compound of formula IV

-   in which R₁, R₂, n, Z and D have the meanings given for the formula    I in claim 1; and X₁ is a leaving group, or, where appropriate, a    tautomer and/or salt thereof with a compound of formula III    HN(R₃)-A-(X)_(p)—(Y)_(q)—B  (III),-   in which R₃, A, X, Y, p, q and B have the meanings given for formula    I, or, where appropriate, with a tautomer and/or salt thereof or,-   c) for the preparation of a compound of formula I, or, where    appropriate, a tautomer and/or salt thereof,-   reacting a compound of formula V

-   in which R₁, R₂, R₃, n, A, X, Y, Z and B have the meanings given for    the formula I in claim 1, or, where appropriate, a tautomer and/or    salt thereof with a compound of formula VI    X₂C(═O)D  (VI),-   in which D has the meaning given for formula I in claim 1; and X₂ is    a leaving group, or, where appropriate, with a tautomer and/or salt    thereof;-   and/or converting a compound of formula I or, where appropriate, a    tautomer thereof, in each case in free form or in salt form, into    another compound of formula I or, where appropriate, a tautomer    thereof, separating an isomer mixture, which can be obtained in    accordance with the process, and isolating the desired isomer and/or    converting a free compound of formula I or, where appropriate, a    tautomer thereof into a salt or a salt of a compound of formula I    or, where appropriate, a tautomer thereof into the free compound of    formula I or, where appropriate, a tautomer thereof or into another    salt.

The compounds of formula II are described in WO 04/111030. The compoundsof formulae III and V are novel and especially developed for thepreparation of the compounds of formula I and constitute therefore afurther embodiment of the present invention. The preferences for thesubstituents of formula I mentioned above are also valid for thecompounds of formulae III and V.

In especially preferred compounds of formula III

-   R₃ is hydrogen;-   A is C₁-C₆alkylene which may be substituted by C₃-C₆cycloalkyl,    C₂-C₆alkenyl, cyano, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl,    C₁-C₄alkoxy, halogen or C₁-C₆haloalkyl; or A is C₃-C₆cycloalkylene;-   p and q are, independently from each other, 0 or 1;-   X is oxygen, NH; NCH₃ or NC₂H₅;-   Y is C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene or,    C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene substituted by    halogen, C₃-C₆cycloalkyl, C₁-C₄alkylsulfonyl or C₁-C₄alkoxy;-   B is cyclopropyl or cyclobutyl which may be mono- di-, or    trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy    or C₁-C₄alkylthio; or B is CH(CH₂O), CH(CHMeO), CH-(CMe₂O),    CH(CH₂S), CH(CH₂OCH₂), CH(CHMeOCH₂), CH(CMe₂OCH₂), CH(CH₂S—(O)₂CH₂),    CH(CHMeS(O)₂CH₂), CH(CMe₂S(O)₂CH₂), C(Me)-(CH₂O), C(Me)(CHMeO),    C(Me)-(CMe₂O), C(Me)-(CH₂S), C(Me)-(CH₂OCH₂), C(Me)(CHMeOCH₂),    C(Me)-(CMe₂OCH₂), C(Me)-(CH₂S(O)₂CH₂), C(Me)-(CHMe-S(O)₂CH₂) or    C(Me)-(CMe₂-S(O)₂CH₂), preferably B is cyclopropyl or cyclobutyl    which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl,    hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio.

In especially preferred compounds of formula V

-   R₁ is C₁-C₄alkyl, halogen, C₁-C₅haloalkyl, nitro, C₁-C₄alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl,    C₁-C₄alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl or    C₁-C₄haloalkylsulfonyl;-   R₂ and R₃ are hydrogen;-   A is C₁-C₆alkylene which may be substituted by C₃-C₆cycloalkyl,    C₂-C₆alkenyl, cyano, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl,    C₁-C₄alkoxy, halogen or C₁-C₆haloalkyl; or A is C₃-C₆cycloalkylene;-   p and q are, independently from each other, 0 or 1;-   X is oxygen, NH; NCH₃ or NC₂H₅;-   Y is C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene or,    C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene substituted by    halogen, C₃-C₆cycloalkyl, C₁-C₄alkylsulfonyl or C₁-C₄alkoxy;-   B is cyclopropyl or cyclobutyl which may be mono- di-, or    trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy    or C₁-C₄alkylthio; or B is CH(CH₂O), CH(CHMeO), CH—(CMe₂O),    CH(CH₂S), CH(CH₂OCH₂), CH(CHMeOCH₂), CH(CMe₂OCH₂), CH(CH₂S—(O)₂CH₂),    CH(CHMeS(O)₂CH₂), CH(CMe₂S(O)₂CH₂), C(Me)-(CH₂O), C(Me)(CHMeO),    C(Me)-(CMe₂O), C(Me)-(CH₂S), C(Me)-(CH₂OCH₂), C(Me)(CHMeOCH₂),    C(Me)-(CMe₂OCH₂), C(Me)-(CH₂S(O)₂CH₂), C(Me)-(CHMe-S(O)₂CH₂) or    C(Me)-(CMe₂-S(O)₂CH₂), preferably B is cyclopropyl or cyclobutyl    which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl,    hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio.

TABLE B Preferred compounds of formula III represented by the formulaIIIa: HN(H)-A-(X)_(p)-(Y)_(q)-B (IIIa), Cpd No. A X Y B B1 CH₂ — —cyclopropyl B2 CHMe — — cyclopropyl B3 C(CH₂CH₂) — — cyclopropyl B4C(CH₂CH₂) — — cyclobutyl B5 CH₂ — — 2,2-dichloro-cyclopropyl B6 CH₂ — —1-methyl-2,2-dichloro-cyclo-propyl B7 CH₂ — — 2,2-dibromo-cyclopropyl B8CH₂ — — 1-methyl-2,2-dibromo-cyclo-propyl B9 CH₂ — —2,2,3,3-tetrafluoro-cyclobutyl B12 CH₂ — — C(SMe)—(CH₂CH₂CH₂) B13 CH₂ —— C(S(O)Me)—(CH₂CH₂CH₂) B14 CH₂ — — C(S(O)₂Me)—(CH₂CH₂CH₂) B15 CH₂ — —cyclobutyl B16 CH₂ — — C(Me)—(CH₂OCH₂) B17 CH₂ — — CH(CMe₂(CH—CH═CMe₂))B18 CH₂ — — C(CH₂OCH₃)—(CH₂OCH₂) B19 CH₂ — — CH(CH₂O) B20 CHCOOMe — —cyclopropyl B21 CH₂ — CH₂ CH(CH₂—CFCl) B22 CH₂ — CH₂ cyclopropyl B23 CH₂— — C(Me)—(CH₂CH₂) B24 CH₂ — — CH(CH₂—CMe₂) B25 CH₂ — — CH(CH₂CH₂O) B26CH₂ — — C(S(O)(NCOCF₃)Me)—(CH₂CH₂CH₂) B27 CH₂ — —C(S(O)(NH)Me)—(CH₂CH₂CH₂) B28 CH₂ — — CH(CMe₂CMe₂) B29 CH₂ — —C(SMe)—(CH₂CH₂) B30 CH₂ — — C(S(O)₂Me)—(CH₂CH₂) B31 CH₂ — —C(CF₃)—(CH₂CH₂) B32 CH₂ — — CH(CH₂—CFCl) B33 CH₂ — — C(S(O)Me)—(CH₂CH₂)B34 CH₂ — — C(S(O)(NCOCF₃)Me)—(CH₂CH₂) B35 CH₂ — —C(S(O)(NH)Me)—(CH₂CH₂) B36 C(CH₂CH₂) — — C(COOEt)—(CH₂CH₂) B37 C(CH₂CH₂)— — C(COOiBr)—(CH₂CH₂) B38 C(CH₂CH₂) — — CH(CH₂—CMe₂) B39 CMe₂ — —cyclopropyl B40 C(CH₂CH₂) — — C(Me)—(CH₂CH₂)

TABLE D Preferred compounds of formula V represented by formula Va: (Va)

Cpd No. R₉₁ R₉₂ A X Y B D1 Me Cl CH₂ — — cyclopropyl D2 Me Cl CHMe — —cyclopropyl D3 Me Cl C(CH₂CH₂) — — cyclopropyl D4 Me Cl C(CH₂CH₂) — —cyclobutyl D5 Me Cl CH₂ — — 2,2-dichloro-cyclopropyl D6 Me Cl CH₂ — —1-methyl-2,2-dichloro- cyclo-propyl D7 Me Cl CH₂ — —2,2-dibromo-cyclopropyl D8 Me Cl CH₂ — — 1-methyl-2,2-dibromo-cyclo-propyl D9 Me Cl CH₂ — — 2,2,3,3-tetrafluoro- cyclobutyl D12 Me ClCH₂ — — C(SMe)-(CH₂CH₂CH₂) D13 Me Cl CH₂ — — C(S(O)Me)-(CH₂CH₂CH₂) D14Me Cl CH₂ — — C(S(O)₂Me)-(CH₂CH₂CH₂) D15 Me Cl CH₂ — — cyclobutyl D16 MeCl CH₂ — — C(Me)-(CH₂OCH₂) D17 Me Cl CH₂ — — CH(CMe₂(CH—CH═CMe₂)) D18 MeCl CH₂ — — C(CH₂OCH₃)-(CH₂OCH₂) D19 Me Cl CH₂ — — CH(CH₂O) D20 Me ClCHCOOMe — — cyclopropyl D21 Me Cl CH₂ — CH₂ CH(CH₂—CFCl) D22 Me Cl CH₂ —CH₂ cyclopropyl D23 Me Cl CH₂ — — C(Me)-(CH₂CH₂) D24 Me Cl CH₂ — —CH(CH₂—CMe₂) D25 Me Cl CH₂ — — CH(CH₂CH₂O) D26 Me Cl CH₂ — —O(S(O)(NCOCF₃)Me)- (CH₂CH₂CH₂) D27 Me Cl CH₂ — — C(S(O)(NH)Me)-(CH₂CH₂CH₂) D28 Me Cl CH₂ — — CH(CMe₂CMe₂) D29 Me Cl CH₂ — —C(SMe)-(CH₂CH₂) D30 Me Cl CH₂ — — C(S(O)₂Me)-(CH₂CH₂) D31 Me Cl CH₂ — —C(CF₃)-(CH₂CH₂) D32 Me Cl CH₂ — — CH(CH₂—CFCl) D33 Me Cl CH₂ — —C(S(O)Me)-(CH₂CH₂) D34 Me Cl CH₂ — — C(S(O)(NCOCF₃)Me)-(CH₂CH₂) D35 MeCl CH₂ — — C(S(O)(NH)Me)-(CH₂CH₂) D36 Me Cl C(CH₂CH₂) — —C(COOEt)-(CH₂CH₂) D37 Me Cl C(CH₂CH₂) — — C(COOiDr)-(CH₂CH₂) D38 Me ClC(CH₂CH₂) — — CH(CH₂—CMe₂) D39 Cl H CH₂ — — cyclopropyl D40 Cl HC(CH₂CH₂) — — cyclopropyl D41 Me H CH₂ — — cyclopropyl D42 Me HC(CH₂CH₂) — — cyclopropyl D43 Me Cl CMe₂ — — cyclopropyl D44 Me ClC(CH₂CH₂) — — C(Me)-(CH₂CH₂) D45 Me 2-pyridyl CH₂ — — cyclopropyl D47 Me2-pyridyl C(CH₂CH₂) — — cyclopropyl D48 Me Cl C(CH₂CH₂) — — cyclopropylD49 Me 3-pyridyl CH₂ — — cyclopropyl D50 Me Cl C(CH₂CH₂) — — cyclopropylD51 Me Cl C(CH₂CH₂) — — cyclopropyl D52 Me NH₂ C(CH₂CH₂) — — cyclopropylD53 Me NH₂ CH₂ — — cyclopropyl D54 Me I C(CH₂CH₂) — — cyclopropyl D55 MeBr CH₂ — — cyclopropyl D56 Me Br CH₂ — — cyclopropyl D57 Me Br C(CH₂CH₂)— — cyclopropyl D58 Me Br CH₂ — — cyclopropyl D59 Me Br C(CH₂CH₂) — —cyclopropyl D60 Me NO₂ CH₂ cyclopropyl D61 Me NO₂ C(CH₂CH₂) cyclopropylD62 Me NO₂ C(CH₂CH₂) cyclopropyl D63 Me NO₂ C(CH₂CH₂) cyclopropyl D64 MeNO₂ C(CH₂CH₂) cyclopropyl D65 Me Cl CH₂ — — cyclobutyl D66 Me Cl CHMe —— cyclobutyl D67 Me Cl CH(CH₂)C — — C(CH₂)₂

Physical data for compounds of formula Va according to Table D:

Compound No. melting point D1 128-129° C. D3 177-178° C.

What has been said above for tautomers and/or salts of compounds Iapplies analogously to starting materials mentioned hereinabove andhereinbelow with regard to the tautomers and/or salts thereof.

The reactions described hereinabove and hereinbelow are carried out in amanner known per se, for example in the absence or, normally, in thepresence of a suitable solvent or diluent or of a mixture of these, theprocess being carried out, as required, with cooling, at roomtemperature or with heating, for example in a temperature range of fromapproximately −80° C. to the boiling point of the reaction mixture,preferably from approximately −20° C. to approximately +150° C., and, ifrequired, in a sealed vessel, under reduced, normal or elevatedpressure, in an inert gas atmosphere and/or under anhydrous conditions.Especially advantageous reaction conditions can be seen from theexamples.

Unless otherwise specified, the starting materials mentioned hereinaboveand hereinbelow, which are used for the preparation of the compounds Ior, where appropriate, the tautomers thereof, in each case in free formor in salt form, are known or can be prepared by methods known per se,for example in accordance with the information given below.

Variant a)

The reactants can be reacted with each other as such, i.e. withoutaddition of a solvent or diluent, for example in the melt. In mostcases, however, it is advantageous to add an inert solvent or diluent ora mixture of these. Examples of such solvents or diluents which may bementioned are: aromatic, aliphatic and alicyclic hydrocarbons andhalohydrocarbons such as benzene, toluene, xylene, mesitylene, tetralin,chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane,cyclohexane, dichloromethane, trichloromethane, tetrachloromethane,dichloroethane, trichloroethene or tetrachloroethene; esters such asethyl acetate; ethers such as diethyl ether, dipropyl ether, diisopropylether, dibutyl ether, tert-butyl methyl ether, ethyleneglycol monomethylether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether,dimethoxydiethyl ether, tetrahydrofuran or dioxane; ketones, such asacetone, methyl ethyl ketone or methyl isobutyl ketone; alcohols, suchas methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol orglycerol; amides such as N,N-di-methylformamide, N,N-diethylformamide,N,N-dimethylacetamide, N-methylpyrrolidone or hexamethylphosphorictriamide; nitriles, such as acetonitrile or propionitrile; andsulfoxides, such as dimethyl sulfoxide.

The reaction is advantageously carried out in a temperature range fromapproximately −80° C. to approximately +140° C., preferably fromapproximately −30° C. to approximately +100° C., in many cases in therange between room temperature and approximately +80° C.

Variant b)

Examples of suitable leaving groups X₁ in the compounds IV are hydroxy,C₁-C₈alkoxy, halo-C₁-C₈alkoxy, C₁-C₈alkanoyloxy, mercapto,C₁-C₈alkylthio, halo-C₁-C₈alkylthio, C₁-C₈alkylsulfonyloxy,halo-C₁-C₈alkylsulfonyloxy, benzenesulfonyloxy, toluenesulfonyloxy andhalogen, such as chlorine. Preferred are hydroxy, C₁-C₈alkoxy andchlorine.

The reactants can be reacted with each other as such, i.e. withoutadding a solvent or diluent. In most cases, however, it is advantageousto add an inert solvent or diluent or a mixture of these. Examples ofsuitable solvents or diluents are of the type described under varianta).

The reaction is advantageously carried out in a temperature range fromapproximately −80° C. to approximately +140° C., preferably fromapproximately −20° C. to approximately +100° C., in many cases in therange between room temperature and the reflux temperature of thereaction mixture.

Variant c)

Examples of suitable leaving groups X₂ in the compounds VI are hydroxy,C₁-C₈alkoxy, halo-C₁-C₈alkoxy, C₁-C₈alkanoyloxy, mercapto,C₁-C₈alkylthio, halo-C₁-C₈alkylthio, C₁-C₈alkylsulfonyloxy,halo-C₁-C₈alkylsulfonyloxy, benzenesulfonyloxy, toluenesulfonyloxy andhalogen, such as chlorine. Preferred are hydroxy and chlorine.

The reactants can be reacted in the presence of a base. Examples ofsuitable bases for facilitating the detachment of HX₂ are alkali metalor alkaline earth metal hydroxides, alkali metal or alkaline earth metalhydrides, alkali metal or alkaline earth metal amides, alkali metal oralkaline earth metal alkoxides, alkali metal or alkaline earth metalacetates, alkali metal or alkaline earth metal carbonates, alkali metalor alkaline earth metal dialkylamides or alkali metal or alkaline earthmetal alkylsilylamides, alkylamines, alkylenediamines, free orN-alkylated saturated or unsaturated cycloalkylamines, basicheterocycles, ammonium hydroxides and carbocyclic amines. Examples whichmay be mentioned are sodium hydroxide, sodium hydride, sodium amide,sodium methoxide, sodium acetate, sodium carbonate, potassiumtert-butoxide, potassium hydroxide, potassium carbonate, potassiumhydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide,calcium hydride, triethylamine, diisopropylethylamine,triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine,N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine,quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

The reactants can be reacted with each other as such, i.e. withoutadding a solvent or diluent. In most cases, however, it is advantageousto add an inert solvent or diluent or a mixture of these. Examples ofsuitable solvents or diluents are of the type described under varianta). If the reaction is carried out in the presence of a base, baseswhich are employed in excess, such as triethylamine, pyridine,N-methylmorpholine or N,N-diethylaniline, may also act as solvents ordiluents.

The reaction is advantageously carried out in a temperature range fromapproximately −80° C. to approximately +140° C., preferably fromapproximately −30° C. to approximately +100° C., in many cases in therange between room temperature and approximately +80° C.

A compound I can be converted in a manner known per se into anothercompound I by replacing one or more substituents of the startingcompound I in the customary manner by (an)other substituent(s) accordingto the invention.

For example,

-   -   in compounds I, in which R₂ is hydrogen, this hydrogen R₂ can be        replaced by a substituent R₂, which is different from hydrogen;        or    -   in compounds I, in which R₃ is hydrogen, this hydrogen R₃ can be        replaced by a substituent R₃, which is different from hydrogen.

Depending on the choice of the reaction conditions and startingmaterials which are suitable in each case, it is possible, for example,in one reaction step only to replace one substituent by anothersubstituent according to the invention, or a plurality of substituentscan be replaced by other substituents according to the invention in thesame reaction step.

Salts of compounds I can be prepared in a manner known per se. Thus, forexample, acid addition salts of compounds I are obtained by treatmentwith a suitable acid or a suitable ion exchanger reagent and salts withbases are obtained by treatment with a suitable base or with a suitableion exchanger reagent.

Salts of compounds I can be converted in the customary manner into thefree compounds I, acid addition salts, for example, by treatment with asuitable basic compound or with a suitable ion exchanger reagent andsalts with bases, for example, by treatment with a suitable acid or witha suitable ion exchanger reagent.

Salts of compounds I can be converted in a manner known per se intoother salts of compounds I, acid addition salts, for example, into otheracid addition salts, for example by treatment of a salt of inorganicacid such as hydrochloride with a suitable metal salt such as a sodium,barium or silver salt, of an acid, for example with silver acetate, in asuitable solvent in which an inorganic salt which forms, for examplesilver chloride, is insoluble and thus precipitates from the reactionmixture.

Depending on the procedure or the reaction conditions, the compounds I,which have salt-forming properties can be obtained in free form or inthe form of salts.

The compounds I and, where appropriate, the tautomers thereof, in eachcase in free form or in salt form, can be present in the form of one ofthe isomers which are possible or as a mixture of these, for example inthe form of pure isomers, such as antipodes and/or diastereomers, or asisomer mixtures, such as enantiomer mixtures, for example racemates,diastereomer mixtures or racemate mixtures, depending on the number,absolute and relative configuration of asymmetric carbon atoms whichoccur in the molecule and/or depending on the configuration ofnon-aromatic double bonds which occur in the molecule; the inventionrelates to the pure isomers and also to all isomer mixtures which arepossible and is to be understood in each case in this sense hereinaboveand hereinbelow, even when stereochemical details are not mentionedspecifically in each case.

Diastereomer mixtures or racemate mixtures of compounds I, in free formor in salt form, which can be obtained depending on which startingmaterials and procedures have been chosen can be separated in a knownmanner into the pure diasteromers or racemates on the basis of thephysicochemical differences of the components, for example by fractionalcrystallization, distillation and/or chromatography.

Enantiomer mixtures, such as racemates, which can be obtained in asimilar manner can be resolved into the optical antipodes by knownmethods, for example by recrystallization from an optically activesolvent, by chromatography on chiral adsorbents, for examplehigh-performance liquid chromatography (HPLC) on acetyl cellulose, withthe aid of suitable microorganisms, by cleavage with specific,immobilized enzymes, via the formation of inclusion compounds, forexample using chiral crown ethers, where only one enantiomer iscomplexed, or by conversion into diastereomeric salts, for example byreacting a basic end-product racemate with an optically active acid,such as a carboxylic acid, for example camphor, tartaric or malic acid,or sulfonic acid, for example camphorsulfonic acid, and separating thediastereomer mixture which can be obtained in this manner, for exampleby fractional crystallization based on their differing solubilities, togive the diastereomers, from which the desired enantiomer can be setfree by the action of suitable agents, for example basic agents.

Pure diastereomers or enantiomers can be obtained according to theinvention not only by separating suitable isomer mixtures, but also bygenerally known methods of diastereoselective or enantioselectivesynthesis, for example by carrying out the process according to theinvention with starting materials of a suitable stereochemistry.

It is advantageous to isolate or synthesize in each case thebiologically more effective isomer, for example enantiomer ordiastereomer, or isomer mixture, for example enantiomer mixture ordiastereomer mixture, if the individual components have a differentbiological activity.

The compounds I and, where appropriate, the tautomers thereof, in eachcase in free form or in salt form, can, if appropriate, also be obtainedin the form of hydrates and/or include other solvents, for example thosewhich may have been used for the crystallization of compounds which arepresent in solid form.

The compounds I according to the invention are preventively and/orcuratively valuable active ingredients in the field of pest control,even at low rates of application, which have a very favorable biocidalspectrum and are well tolerated by warm-blooded species, fish andplants. The active ingredients according to the invention act againstall or individual developmental stages of normally sensitive, but alsoresistant, animal pests, such as insects or representatives of the orderAcarina. The insecticidal or acaricidal activity of the activeingredients according to the invention can manifest itself directly,i.e. in destruction of the pests, which takes place either immediatelyor only after some time has elapsed, for example during ecdysis, orindirectly, for example in a reduced oviposition and/or hatching rate, agood activity corresponding to a destruction rate (mortality) of atleast 50 to 60%.

Examples of the abovementioned animal pests are:

-   from the order Acarina, for example,-   Acarus siro, Aceria sheldoni, Aculus schlechtendali, Amblyomma spp.,    Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa,    Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae,    Eotetranychus carpini, Eriophyes spp., Hyalomma spp., Ixodes spp.,    Olygonychus pratensis, Ornithodoros spp., Panonychus spp.,    Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp.,    Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Tarsonemus    spp. and Tetranychus spp.;-   from the order Anoplura, for example,-   Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp.    and Phylloxera spp.;-   from the order Coleoptera, for example,-   Agriotes spp., Anthonomus spp., Atomaria linearis, Chaetocnema    tibialis, Cosmopolites spp., Curculio spp., Dermestes spp.,    Diabrotica spp., Epilachna spp., Eremnus spp., Leptinotarsa    decemlineata, Lissorhoptrus spp., Melolontha spp., Orycaephilus    spp., Otiorhynchus spp., Phlyctinus spp., Popillia spp., Psylliodes    spp., Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga    spp., Tenebrio spp., Tribolium spp. and Trogoderma spp.;-   from the order Diptera, for example,-   Aedes spp., Antherigona soccata, Bibio hortulanus, Calliphora    erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp.,    Cuterebra spp., Dacus spp., Drosophila melanogaster, Fannia spp.,    Gastrophilus spp., Glossina spp., Hypoderma spp., Hyppobosca spp.,    Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp.,    Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami,    Phorbia spp., Rhagoletis pomonella, Sciara spp., Stomoxys spp.,    Tabanus spp., Tannia spp. and Tipula spp.;    from the order Heteroptera, for example,-   Cimex spp., Distantiella theobroma, Dysdercus spp., Euchistus spp.,    Eurygaster spp., Leptocorisa spp., Nezara spp., Piesma spp.,    Rhodnius spp., Sahlbergella singularis, Scotinophara spp. and    Triatoma spp.;-   from the order Homoptera, for example,-   Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella spp.,    Aphididae, Aphis spp., Aspidiotus spp., Bemisia tabaci, Ceroplaster    spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Coccus    hesperidum, Empoasca spp., Eriosoma larigerum, Erythroneura spp.,    Gascardia spp., Laodelphax spp., Lecanium corni, Lepidosaphes spp.,    Macrosiphus spp., Myzus spp., Nephotettix spp., Nilaparvata spp.,    Parlatoria spp., Pemphigus spp., Planococcus spp., Pseudaulacaspis    spp., Pseudococcus spp., Psylla spp., Pulvinaria aethiopica,    Quadraspidiotus spp., Rhopalosiphum spp., Saissetia spp.,    Scaphoideus spp., Schizaphis spp., Sitobion spp., Trialeurodes    vaporariorum, Trioza erytreae and Unaspis citri;-   from the order Hymenoptera, for example,-   Acromyrmex, Atta spp., Cephus spp., Diprion spp., Diprionidae,    Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium    pharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp.;-   from the order Isoptera, for example,-   Reticulitermes spp.;-   from the order Lepidoptera, for example,-   Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama    argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp.,    Argyrotaenia spp., Autographa spp., Busseola fusca, Cadra cautella,    Carposina nipponensis, Chilo spp., Choristoneura spp., Clysia    ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp.,    Coleophora spp., Crocidolomia binotalis, Cryptophlebia leucotreta,    Cydia spp., Diatraea spp., Diparopsis castanea, Earias spp.,    Ephestia spp., Eucosma spp., Eupoecilia ambiguella, Euproctis spp.,    Euxoa spp., Grapholita spp., Hedya nubiferana, Heliothis spp.,    Hellula undalis, Hyphantria cunea, Keiferia lycopersicella,    Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Lymantria    spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca    sexta, Operophtera spp., Ostrinia nubilalis, Pammene spp., Pandemis    spp., Panolis flammea, Pectinophora gossypiela, Phthorimaea    operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays    spp., Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera    spp., Synanthedon spp., Thaumetopoea spp., Tortrix spp.,    Trichoplusia ni and Yponomeuta spp.;-   from the order Mallophaga, for example,-   Damalinea spp. and Trichodectes spp.;-   from the order Orthoptera, for example,-   Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae,    Locusta spp., Periplaneta spp. and Schistocerca spp.;-   from the order Psocoptera, for example,-   Liposcelis spp.;-   from the order Siphonaptera, for example,-   Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis;-   from the order Thysanoptera, for example,-   Frankliniella spp., Hercinothrips spp., Scirtothrips aurantii,    Taeniothrips spp., Thrips palmi and Thrips tabaci; and-   from the order Thysanura, for example,-   Lepisma saccharina.

The active ingredients according to the invention can be used forcontrolling, i.e. containing or destroying, pests of the abovementionedtype which occur in particular on plants, especially on useful plantsand ornamentals in agriculture, in horticulture and in forests, or onorgans, such as fruits, flowers, foliage, stalks, tubers or roots, ofsuch plants, and in some cases even plant organs which are formed at alater point in time remain protected against these pests.

Suitable target crops are, in particular, cereals, such as wheat,barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodderbeet; fruit, for example pomaceous fruit, stone fruit or soft fruit,such as apples, pears, plums, peaches, almonds, cherries or berries, forexample strawberries, raspberries or blackberries; leguminous crops,such as beans, lentils, peas or soya; oil crops, such as oilseed rape,mustard, poppies, olives, sunflowers, coconut, castor, cocoa or groundnuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants,such as cotton, flax, hemp or jute; citrus fruit, such as oranges,lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce,asparagus, cabbages, carrots, onions, tomatoes, potatoes or bellpeppers; Lauraceae, such as avocado, Cinnamonium or camphor; and alsotobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines,hops, the plantain family, latex plants and ornamentals.

The active ingredients according to the invention are especiallysuitable for controlling Aphis craccivora, Diabrotica balteata,Heliothis virescens, Myzus persicae, Plutella xylostella and Spodopteralittoralis in cotton, vegetable, maize, rice and soya crops. The activeingredients according to the invention are further especially suitablefor controlling Mamestra (preferably in vegetables), Cydia pomonella(preferably in apples), Empoasca (preferably in vegetables, vineyards),Leptinotarsa (preferably in potatoes) and Chilo supressalis (preferablyin rice).

The term “crops” is to be understood as including also crops that havebeen rendered tolerant to herbicides like bromoxynil or classes ofherbicides (such as, for example, HPPD inhibitors, ALS inhibitors, forexample primisulfuron, prosulfuron and trifloxysulfuron, EPSPS(5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS(glutamine synthetase) inhibitors) as a result of conventional methodsof breeding or genetic engineering. An example of a crop that has beenrendered tolerant to imidazolinones, e.g. imazamox, by conventionalmethods of breeding (mutagenesis) is Clearfield® summer rape (Canola).Examples of crops that have been rendered tolerant to herbicides orclasses of herbicides by genetic engineering methods include glyphosate-and glufosinate-resistant maize varieties commercially available underthe trade names RoundupReady®, Herculex I® and LibertyLink®.

The term “crops” is to be understood as including also crop plants whichhave been so transformed by the use of recombinant DNA techniques thatthey are capable of synthesising one or more selectively acting toxins,such as are known, for example, from toxin-producing bacteria,especially those of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, forexample, insecticidal proteins, for example insecticidal proteins fromBacillus cereus or Bacillus popliae; or insecticidal proteins fromBacillus thuringiensis, such as δ-endotoxins, e.g. CryIA(b), CryIA(c),CryIF, CryIF(a2), CryIIA(b), CryIIA, CryIIB(b1) or Cry9c, or vegetativeinsecticidal proteins (VIP), e.g. VIP1, VIP2, VIP3 or VIP3A; orinsecticidal proteins of bacteria colonising nematodes, for examplePhotorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens,Xenorhabdus nematophilus; toxins produced by animals, such as scorpiontoxins, arachnid toxins, wasp toxins and other insect-specificneurotoxins; toxins produced by fungi, such as Streptomycetes toxins,plant lectins, such as pea lectins, barley lectins or snowdrop lectins;agglutinins; proteinase inhibitors, such as trypsine inhibitors, serineprotease inhibitors, patatin, cystatin, papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ionchannel blockers, such as blockers of sodium or calcium channels,juvenile hormone esterase, diuretic hormone receptors, stilbenesynthase, bibenzyl synthase, chitinases and glucanases.

In the context of the present invention there are to be understood byδ-endotoxins, for example CryIA(b), CryIA(c), CryIF, CryIF(a2),CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c, or vegetative insecticidalproteins (VIP), for example VIP1, VIP2, VIP3 or VIP3A, expressly alsohybrid toxins, truncated toxins and modified toxins. Hybrid toxins areproduced recombinantly by a new combination of different domains ofthose proteins (see, for example, WO 02/15701). Truncated toxins, forexample a truncated CryIA(b), are known. In the case of modified toxins,one or more amino acids of the naturally occurring toxin are replaced.In such amino acid replacements, preferably non-naturally presentprotease recognition sequences are inserted into the toxin, such as, forexample, in the case of CryIIIA055, a cathepsin-D-recognition sequenceis inserted into a CryIIIA toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesisingsuch toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278,WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants aregenerally known to the person skilled in the art and are described, forexample, in the publications mentioned above. CryI-type deoxyribonucleicacids and their preparation are known, for example, from WO 95/34656,EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plantstolerance to harmful insects. Such insects can occur in any taxonomicgroup of insects, but are especially commonly found in the beetles(Coleoptera), two-winged insects (Diptera) and butterflies(Lepidoptera).

Transgenic plants containing one or more genes that code for aninsecticidal resistance and express one or more toxins are known andsome of them are commercially available. Examples of such plants are:YieldGard® (maize variety that expresses a CryIA(b) toxin); YieldGardRootworm® (maize variety that expresses a CryIIIB(b1) toxin); YieldGardPlus® (maize variety that expresses a CryIA(b) and a CryIIB(b1) toxin);Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I®(maize variety that expresses a CryIF(a2) toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to theherbicide glufosinate ammonium); NuCOTN 33B® (cotton variety thatexpresses a CryIA(c) toxin); Boligard I® (cotton variety that expressesa CryIA(c) toxin); Boligard II® (cotton variety that expresses aCryIA(c) and a CryIIA(b) toxin); VIPCOT® (cotton variety that expressesa VIP toxin); NewLeaf® (potato variety that expresses a CryIIA toxin);Nature-Gard® Agrisure® GT Advantage (GA21 glyphosate-tolerant trait),Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

-   1. Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31    790 St. Sauveur, France, registration number C/FR/96/05/10.    Genetically modified Zea mays which has been rendered resistant to    attack by the European corn borer (Ostrinia nubilalis and Sesamia    nonagrioides) by transgenic expression of a truncated CryIA(b)    toxin. Bt11 maize also transgenically expresses the enzyme PAT to    achieve tolerance to the herbicide glufosinate ammonium.-   2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31    790 St. Sauveur, France, registration number C/FR/96/05/10.    Genetically modified Zea mays which has been rendered resistant to    attack by the European corn borer (Ostrinia nubilalis and Sesamia    nonagrioides) by transgenic expression of a CryIA(b) toxin. Bt176    maize also transgenically expresses the enzyme PAT to achieve    tolerance to the herbicide glufosinate ammonium.-   3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I′Hobit 27, F-31    790 St. Sauveur, France, registration number C/FR/96/05/10. Maize    which has been rendered insect-resistant by transgenic expression of    a modified CryIIIA toxin. This toxin is Cry3A055 modified by    insertion of a cathepsin-D-protease recognition sequence. The    preparation of such transgenic maize plants is described in WO    03/018810.-   4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de    Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9.    MON 863 expresses a CryIIIB(b1) toxin and has resistance to certain    Coleoptera insects.-   5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de    Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02.-   6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7    B-1160 Brussels, Belgium, registration number C/NL/00/10.    Genetically modified maize for the expression of the protein CryI F    for achieving resistance to certain Lepidoptera insects and of the    PAT protein for achieving tolerance to the herbicide glufosinate    ammonium.-   7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de    Tervuren, B-1150 Brussels, Belgium, registration number    C/GB/02/M3/03. Consists of conventionally bred hybrid maize    varieties by crossing the genetically modified varieties NK603 and    MON 810. NK603×MON 810 Maize transgenically expresses the protein    CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts    tolerance to the herbicide Roundup® (contains glyphosate), and also    a CryIA(b) toxin obtained from Bacillus thuringiensis subsp.    kurstaki which brings about tolerance to certain Lepidoptera,    include the European corn borer.

Transgenic crops of insect-resistant plants are also described in BATS(Zentrum für Biosicherheit und Nachhaltigkeit, Zentrum BATS,Clarastrasse 13, 4058 Basel, Switzerland) Report 2003, (http://bats.ch).

The term “crops” is to be understood as including also crop plants whichhave been so transformed by the use of recombinant DNA techniques thatthey are capable of synthesising antipathogenic substances having aselective action, such as, for example, the so-called“pathogenesis-related proteins” (PRPs, see e.g. EP-A-0 392 225).Examples of such antipathogenic substances and transgenic plants capableof synthesising such antipathogenic substances are known, for example,from EP-A-0 392 225, WO 95/33818, and EP-A-0 353 191. The methods ofproducing such transgenic plants are generally known to the personskilled in the art and are described, for example, in the publicationsmentioned above.

Antipathogenic substances which can be expressed by such transgenicplants include, for example, ion channel blockers, such as blockers forsodium and calcium channels, for example the viral KP1, KP4 or KP6toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases;the so-called “pathogenesis-related proteins” (PRPs; see e.g. EP-A-0 392225); antipathogenic substances produced by microorganisms, for examplepeptide antibiotics or heterocyclic antibiotics (see e.g. WO 95/33818)or protein or polypeptide factors involved in plant pathogen defence(so-called “plant disease resistance genes”, as described in WO03/000906).

Further areas of use of the compositions according to the invention arethe protection of stored goods and storerooms and the protection of rawmaterials, such as wood, textiles, floor coverings or buildings, andalso in the hygiene sector, especially the protection of humans,domestic animals and productive livestock against pests of the mentionedtype.

In the hygiene sector, the compositions according to the invention areactive against ectoparasites such as hard ticks, soft ticks, mangemites, harvest mites, flies (biting and licking), parasitic fly larvae,lice, hair lice, bird lice and fleas.

Examples of Such Parasites are:

-   Of the order Anoplurida: Haematopinus spp., Linognathus spp.,    Pediculus spp. and Phtirus spp., Solenopotes spp.-   Of the order Mallophagida: Trimenopon spp., Menopon spp., Trinoton    spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina    spp., Trichodectes spp. and Felicola spp.-   Of the order Diptera and the suborders Nematocerina and    Brachycerina, for example Aedes spp., Anopheles spp., Culex spp.,    Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,    Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp.,    Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca    spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp.,    Fannia spp., Glossina spp., Calliphora spp., Lucilia spp.,    Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp.,    Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp.    and Melophagus spp.-   Of the order Siphonapterida, for example Pulex spp., Ctenocephalides    spp., Xenopsylla spp., Ceratophyllus spp.-   Of the order Heteropterida, for example Cimex spp., Triatoma spp.,    Rhodnius spp., Panstrongylus spp.-   Of the order Blattarida, for example Blatta orientalis, Periplaneta    americana, Blattelagermanica and Supella spp.    Of the subclass Acaria (Acarida) and the orders Meta- and    Meso-stigmata, for example Argas spp., Ornithodorus spp., Otobius    spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,    Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus    spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and    Varroa spp.-   Of the orders Actinedida (Prostigmata) and Acaridida (Astigmata),    for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp.,    Myobia spp., Psorergates spp., Demodex spp., Trombicula spp.,    Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp.,    Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp.,    Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp.,    Cytodites spp. and Laminosioptes spp.

The compositions according to the invention are also suitable forprotecting against insect infestation in the case of materials such aswood, textiles, plastics, adhesives, glues, paints, paper and card,leather, floor coverings and buildings.

The compositions according to the invention can be used, for example,against the following pests: beetles such as Hylotrupes bajulus,Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum,Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobiumcarpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctuslinearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis,Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychuscapucins, Heterobostrychus brunneus, Sinoxylon spec. and Dinoderusminutus, and also hymenopterans such as Sirex juvencus, Urocerus gigas,Urocerus gigas taignus and Urocerus augur, and termites such asKalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis andCoptotermes formosanus, and bristletails such as Lepisma saccharina.

The invention therefore also relates to pesticidal compositions such asemulsifiable concentrates, suspension concentrates, directly sprayableor dilutable solutions, spreadable pastes, dilute emulsions, solublepowders, dispersible powders, wettable powders, dusts, granules orencapsulations in polymeric substances, which comprise—at least—one ofthe active ingredients according to the invention and which are to beselected to suit the intended aims and the prevailing circumstances.

In these compositions, the active ingredient is employed in pure form, asolid active ingredient for example in a specific particle size, or,preferably, together with—at least—one of the auxiliaries conventionallyused in the art of formulation, such as extenders, for example solventsor solid carriers, or such as surface-active compounds (surfactants).

Examples of suitable solvents are: unhydrogenated or partiallyhydrogenated aromatic hydrocarbons, preferably the fractions C₈ to C₁₂of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes ortetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such asparaffins or cyclohexane, alcohols such as ethanol, propanol or butanol,glycols and their ethers and esters such as propylene glycol,dipropylene glycol ether, ethylene glycol or ethylene glycol monomethylether or ethylene glycol monoethyl ether, ketones, such ascyclohexanone, isophorone or diacetone alcohol, strongly polar solvents,such as N-methylpyrrolid-2-one, dimethyl sulfoxide orN,N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils,such as unexpodized or epoxidized rapeseed, castor, coconut or soya oil,and silicone oils.

Solid carriers which are used for example for dusts and dispersiblepowders are, as a rule, ground natural minerals such as calcite, talc,kaolin, montmorillonite or attapulgite. To improve the physicalproperties, it is also possible to add highly disperse silicas or highlydisperse absorbtive polymers. Suitable particulate adsorptive carriersfor granules are porous types, such as pumice, brick grit, sepiolite orbentonite, and suitable non-sorptive carrier materials are calcite orsand. In addition, a large number of granulated materials of inorganicor organic nature can be used, in particular dolomite or comminutedplant residues.

Suitable surface-active compounds are, depending on the type of theactive ingredient to be formulated, non-ionic, cationic and/or anionicsurfactants or surfactant mixtures which have good emulsifying,dispersing and wetting properties. The surfactants mentioned below areonly to be considered as examples; a large number of further surfactantswhich are conventionally used in the art of formulation and suitableaccording to the invention are described in the relevant literature.

Suitable non-ionic surfactants are, especially, polyglycol etherderivatives of aliphatic or cycloaliphatic alcohols, of saturated orunsaturated fatty acids or of alkyl phenols which may containapproximately 3 to approximately 30 glycol ether groups andapproximately 8 to approximately 20 carbon atoms in the (cyclo)aliphatichydrocarbon radical or approximately 6 to approximately 18 carbon atomsin the alkyl moiety of the alkyl phenols. Also suitable arewater-soluble polyethylene oxide adducts with polypropylene glycol,ethylenediaminopolypropylene glycol or alkyl polypropylene glycol having1 to approximately 10 carbon atoms in the alkyl chain and approximately20 to approximately 250 ethylene glycol ether groups and approximately10 to approximately 100 propylene glycol ether groups. Normally, theabovementioned compounds contain 1 to approximately 5 ethylene glycolunits per propylene glycol unit. Examples which may be mentioned arenonylphenoxypolyethoxyethanol, castor oil polyglycol ether,polypropylene glycol/polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol oroctylphenoxypolyethoxyethanol. Also suitable are fatty acid esters ofpolyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

The cationic surfactants are, especially, quarternary ammonium saltswhich generally have at least one alkyl radical of approximately 8 toapproximately 22 C atoms as substituents and as further substituents(unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzylradicals. The salts are preferably in the form of halides,methylsulfates or ethylsulfates. Examples are stearyltrimethylammoniumchloride and benzylbis(2-chloroethyl)ethyl-ammonium bromide.

Examples of suitable anionic surfactants are water-soluble soaps orwater-soluble synthetic surface-active compounds. Examples of suitablesoaps are the alkali, alkaline earth or (un-substituted or substituted)ammonium salts of fatty acids having approximately 10 to approximately22 C atoms, such as the sodium or potassium salts of oleic or stearicacid, or of natural fatty acid mixtures which are obtainable for examplefrom coconut or tall oil; mention must also be made of the fatty acidmethyl taurates. However, synthetic surfactants are used morefrequently, in particular fatty sulfonates, fatty sulfates, sulfonatedbenzimidazole derivatives or alkylaryl sulfonates. As a rule, the fattysulfonates and fatty sulfates are pre-sent as alkali, alkaline earth or(substituted or unsubstituted) ammonium salts and they generally have analkyl radical of approximately 8 to approximately 22 C atoms, alkyl alsoto be understood as including the alkyl moiety of acyl radicals;examples which may be mentioned are the sodium or calcium salts oflignosulfonic acid, of the dodecylsulfuric ester or of a fatty alcoholsulfate mixture prepared from natural fatty acids. This group alsoincludes the salts of the sulfuric esters and sulfonic acids of fattyalcohol/ethylene oxide adducts. The sulfonated benzimidazole derivativespreferably contain 2 sulfonyl groups and a fatty acid radical ofapproximately 8 to approximately 22 C atoms. Examples ofalkylarylsulfonates are the sodium, calcium or triethanolammonium saltsof decylbenzenesulfonic acid, of dibutyl-naphthalenesulfonic acid or ofa naphthalenesulfonic acid/formaldehyde condensate. Also possible are,furthermore, suitable phosphates, such as salts of the phosphoric esterof a p-nonylphenol/(4-14)ethylene oxide adduct, or phospholipids.

As a rule, the compositions comprise 0.1 to 99%, especially 0.1 to 95%,of active ingredient and 1 to 99.9%, especially 5 to 99.9%, of at leastone solid or liquid adjuvant, it being possible as a rule for 0 to 25%,especially 0.1 to 20%, of the composition to be surfactants (% in eachcase meaning percent by weight). Whereas concentrated compositions tendto be preferred for commercial goods, the end consumer as a rule usesdilute compositions which have substantially lower concentrations ofactive ingredient. Preferred compositions are composed in particular asfollows (%=percent by weight):

Emulsifiable concentrates: active ingredient:   1 to 95%, preferably 5to 20% surfactant:   1 to 30%, preferably 10 to 20% solvent:   5 to 98%,preferably 70 to 85% Dusts: active ingredient:  0.1 to 10%, preferably0.1 to 1% solid carrier: 99.9 to 90%, preferably 99.9 to 99% Suspensionconcentrates: active ingredient:   5 to 75%, preferably 10 to 50% water:  94 to 24%, preferably 88 to 30% surfactant:   1 to 40%, preferably 2to 30% Wettable powders: active ingredient:  0.5 to 90%, preferably 1 to80% surfactant:  0.5 to 20%, preferably 1 to 15% solid carrier:   5 to99%, preferably 15 to 98% Granulates: active ingredient:  0.5 to 30%,preferably 3 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%

The compositions can also comprise further solid or liquid auxiliaries,such as stabilizers, for example unepoxidized or epoxidized vegetableoils (for example epoxidized coconut oil, rapeseed oil or soya oil),antifoams, for example silicone oil, preservatives, viscosityregulators, binders and/or tackifiers, fertilizers or other activeingredients for achieving specific effects, for example bactericides,fungicides, nematocides, plant activators, molluscicides or herbicides.

The compositions according to the invention are prepared in a mannerknown per se, in the absence of auxiliaries for example by grinding,screening and/or compressing a solid active ingredient and in thepresence of at least one auxiliary for example by intimately mixingand/or grinding the active ingredient with the auxiliary (auxiliaries).These processes for the preparation of the compositions and the use ofthe compounds I for the preparation of these compositions are also asubject of the invention.

The application methods for the compositions, that is the methods ofcontrolling pests of the abovementioned type, such as spraying,atomizing, dusting, brushing on, dressing, scattering or pouring—whichare to be selected to suit the intended aims of the prevailingcircumstances—and the use of the compositions for controlling pests ofthe abovementioned type are other subjects of the invention. Typicalrates of concentration are between 0.1 and 1000 ppm, preferably between0.1 and 500 ppm, of active ingredient. The rate of application perhectare is generally 1 to 2000 g of active ingredient per hectare, inparticular 10 to 1000 g/ha, preferably 10 to 600 g/ha.

A preferred method of application in the field of crop protection isapplication to the foliage of the plants (foliar application), it beingpossible to select frequency and rate of application to match the dangerof infestation with the pest in question. Alternatively, the activeingredient can reach the plants via the root system (systemic action),by drenching the locus of the plants with a liquid composition or byincorporating the active ingredient in solid form into the locus of theplants, for example into the soil, for example in the form of granules(soil application). In the case of paddy rice crops, such granules canbe metered into the flooded paddy-field.

The compositions according to the invention are also suitable for theprotection of plant propagation material, for example seeds, such asfruit, tubers or kernels, or nursery plants, against pests of theabovementioned type. The propagation material can be treated with thecompositions prior to planting, for example seed can be treated prior tosowing. Alternatively, the compositions can be applied to seed kernels(coating), either by soaking the kernels in a liquid composition or byapplying a layer of a solid composition. It is also possible to applythe compositions when the propagation material is planted to the site ofapplication, for example into the seed furrow during drilling. Thesetreatment methods for plant propagation material and the plantpropagation material thus treated are further subjects of the invention.

PREPARATION EXAMPLES Example H1 Preparation ofN-(4-chloro-2-methyl-6-[([oxetan-2-ylmethyl]amino)carbonyl]phenyl)-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide(Compound P25)

Step 1: Preparation of 2-(phtalimidomethyl)oxetane:

A solution of 2-(tosyloxymethyl)oxetane (27 g, 111.4 mmol) (preparedaccording to A. O. Fitton et al., Synthesis 1987, (12), 1140-2) andpotassium phtalimide (20.64 g, 111.4 mmol) in DMF (200 ml) is stirred ata temperature of 120° C. for 18 hours, then evaporated in vacuo. Theresidue is taken up in ethyl acetate, the organic layer washed withwater and brine, dried (Na2SO4), filtered, and evaporated to dryness.The crude solid product (19.8 g, 82%) is used in the next step withoutfurther purification.

Step 2: Preparation of 2-aminomethyloxetane:

To a solution of 2-(phtalimidomethyl)oxetane (the product of step 1) (19g, 87.5 mmol) in ethanol (250 ml) is added hydrazine hydrate (6.56 g,131.2 mmol) and the reaction mixture is heated to reflux for 30 minutes.The resulting precipitates are filtered off, a small amount of Raney Ni(W-2) added to the filtrate, and the mixture further refluxed for 1.5hours. The inorganic materials are filtered off, and the filtrate wasconcentrated carefully under reduced pressure. The residue is distilledin vacuo to give a colorless liquid (3.63 g, ˜47%), b.p. 55-60° C./30mbar. Contaminated with ethanol and DMF, the product is used in the nextstep without further purification.

Step 3: Preparation of Compound P25:

To a solution of6-chloro-2-[1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one(200 mg, 0.45 mmol) (prepared according to WO 02/48115, example 2D) intetrahydrofurane (4 ml), is added 2-aminomethyloxetane (the product ofstep 2) (79 mg, 0.91 mmol), and the mixture is heated to reflux for 30minutes. The solution is allowed to cool to ambient temperature and thesolvent evaporated in vacuo. The residue is purified by prep. HPLC(hexane/ethyl acetate gradient on LiChrospher Si 60, Merck NW25 column)to afford 180 mg (71%) of the title compound as a white solid. [¹H-NMR(CDCl₃): 10.21 (s, 1H), 8.48 (d, 1H), 7.88 (d, 1H), 7.41 (m, 1H), 7.32(s, 1H), 7.29 (m, 2H), 6.63 (m, 1H), 4.98 (m, 1H), 4.68 (m, 1H), 4.48(m, 1H), 3.71 (m, 1H), 3.59 (m, 1H), 2.68 (m, 1H), 2.43 (m, 1H), 2.19(s, 3H); MS (electrospray ES+): 528, 530 ((M+H)⁺)].

Preparation of the Intermediate bicyclopropyl-1-ylamine:

93.2 ml (328 mmol) Ti(OiPr)₄ is added to a solution of 20 g (298 mmol)cyclopropane carbonitrile in 300 ml ether. The solution is cooled downto a temperature of −78° C. and 199 ml (596 mmol) ethylmagnesium bromidesolution (3 M in ether) is slowly added. After 10 min at −78° C., theslurry is allowed to warm up to ambient temperature and stirred for 1hour. 84.6 g (595 mmol) BF₃.OEt₂ is added and the mixture is stirred atambient temperature for 18 hours. To this mixture, 600 ml NaOH 2N isslowly added at a temperature of 0° C. The organic phase is separatedand extracted with 600 ml HCl 2N. The water phase is evaporated and theresidue is triturated in ether to afford 30.9 g (78%) of the titlecompound as an hydrochloride salt.

The compounds listed in the following Tables P, P′ and A can be preparedanalogous to the procedures described above (m.p.=melting point in °C.): If no definition for substituent X is given, then p is 0, if X is asubstituent, then p is 1. If no definition for substituent Y is given,then q is 0, if Y is a substituent, then q is 1. The group C(CH₂CH₂) forthe substituent A means cyclopropyl with two free valences:

Designations for substituent B like CH(CH₂O), CH(CHMeO), CH—(CMe₂O),CH(CH₂S), CH(CH₂OCH₂), CH(CHMeOCH₂), CH(CMe₂OCH₂), CH(CH₂S—(O)₂CH₂),CH(CHMeS(O)₂CH₂), CH(CMe₂S(O)₂CH₂), C(Me)-(CH₂O), C(Me)-(CHMeO),C(Me)-(CMe₂O), C(Me)-(CH₂S), C(Me)-(CH₂OCH₂), C(Me)-(CH-MeOCH₂),C(Me)-(CMe₂OCH₂), C(Me)-(CH₂S(O)₂CH₂), C(Me)-(CHMe-S(O)₂CH₂) orC(Me)-(CMe₂-S(O)₂CH₂) define cyclic rings. For example, CH(CH₂O) is

C(Me)-(CH-MeO) is

andC(Me)-(CHMe-S(O)₂CH₂) is

TABLE P Compounds of formula Ia: (Ia)

Cpd No. R₉₁ R₉₂ R₉₃ A X Y B Phys. Data P1 Me Cl CF₃ CH₂ — — cyclopropylMS (−ve) 510 (M − 1)⁻ P2 Me Cl CF₃ CHMe — — cyclopropyl MS (+ve) 525(M⁺) MS (−ve) 524 (M − H)⁻ P3 Me Cl CF₃ C(CH₂CH₂) — — cyclopropyl MS(−ve) 536 (M − H)⁻ P4 Me Cl CF₃ C(CH₂CH₂) — — cyclobutyl MS (−ve) 550 (M− H)⁻ P5 Me Cl CF₃ CH₂ — — 2,2-dichloro- MS (−ve) cyclopropyl 580 (M −H)⁻ P6 Me Cl CF₃ CH₂ — — 1-methyl-2,2- MS (−ve) dichloro-cyclo- 594 (M −H)⁻ propyl P7 Me Cl CF₃ CH₂ — — 2,2-dibromo- MS (−ve) cyclopropyl 668 (M− H)⁻ P8 Me Cl CF₃ CH₂ — — 1-methyl-2,2- MS (−ve) dibromo-cyclo- 682 (M− H)⁻ propyl P9 Me Cl CF₃ CH₂ — — 2,2,3,3- MS (−ve) tetrafluoro- 597 (M− H)⁻ cyclobutyl P10 Me Cl Br CH₂ — — cyclopropyl 218-220° C. P11 Me ClCl CH₂ — — cyclopropyl 218-219° C. P12 Me Cl CF₃ CH₂ — — C(SMe)- MS(ES+) (CH₂CH₂CH₂) 572/574 (M + H)⁺ P13 Me Cl CF₃ CH₂ — — C(S(O)Me)-223-224° C. (CH₂CH₂CH₂) P14 Me Cl CF₃ CH₂ — — C(S(O)₂Me)- >250° C.(CH₂CH₂CH₂) MS (ES+) 604/606 (M + H)⁺ P15 Me Cl CF₃ CH₂ — — cyclobutyl206-208° C. P16 Me Cl CF₃ CH₂ — — C(Me)- 201-203° C. (CH₂OCH₂) P17 Me ClCF₃ CH₂ — — CH(CMe₂(CH—CH═CMe₂)) 178-179° C. P18 Me Cl CF₃ CH₂ — —C(CH₂OCH₃)- 190-192° C. (CH₂OCH₂) P19 Me Cl CF₃ CH2 — — CH(CH₂O) MS(ES+) 514/516 (M + H)⁺ P20 Me Cl CF₃ CHCOOMe — — cyclopropyl MS (ES−)568 (M − H)⁻ P21 Me Cl CF₃ CH₂ — CH₂ CH(CH₂—CFCl) 154-156° C. P22 Me ClCF₃ CH₂ — CH₂ cyclopropyl 122-124° C. P23 Me Cl CF₃ CH₂ — —C(Me)-(CH₂CH₂) 208-210° C. P24 Me Cl CF₃ CH₂ — — CH(CH₂—CMe₂) MS (ES+)540/542 (M + H)⁺ P25 Me Cl CF₃ CH₂ — — CH(CH₂CH₂O) MS (ES+) 528/530 (M +H)⁺ P26 Me Cl CF₃ CH₂ — — C(S(O)(NCOCF₃)Me- MS(ES+) (CH₂CH₂CH₂) 699/701(M + H)⁺ P27 Me Cl CF₃ CH₂ — — C(S(O)(NH)Me)- MS (ES+) (CH₂CH₂CH₂)603/605 (M + H)⁺ P28 Me Cl CF₃ CH₂ — — CH(CMe₂CMe₂) 206-208° C. P29 MeCl CF₃ CH₂ — — C(SMe)-(CH₂CH₂) 214-215° C. P30 Me Cl CF₃ CH₂ — —C(S(O)₂Me)- 212-214° C. (CH₂CH₂) P31 Me Cl CF₃ CH₂ — — C(CF₃)-(CH₂CH₂)198-200° C. P32 Me Cl CF₃ CH₂ — — CH(CH₂—CFCl) 228-229° C. P33 Me Cl CF₃CH₂ — — C(S(O)Me)- 212-214° C. (CH₂CH₂) P34 Me Cl CF₃ CH₂ — —C(S(O)(NCOCF₃)Me)- 210-212° C. (CH₂CH₂) P35 Me Cl CF₃ CH₂ — —C(S(O)(NH)Me)- 208-210° 0.C (CH₂CH₂) P36 Me Cl CF₃ C(CH₂CH₂) — —C(COOEt)- 212-213° C. (CH₂CH₂) P37 Me Cl CF₃ C(CH₂CH₂) — — C(COOiPr)-215-217° C. (CH₂CH₂) P38 Me Cl CF₃ C(CH₂CH₂) — — CH(CH₂—CMe₂) MS (ES+)566/568 (M + H)⁺ P39 Cl H CF₃ CH₂ — — cyclopropyl 222-223° C. P40 Cl HCF₃ C(CH₂CH₂) — — cyclopropyl 233-235° C. P41 Me H CF₃ CH₂ — —cyclopropyl 183-185° C. P42 Me H CF₃ C(CH₂CH₂) — — cyclopropyl 232-233°C. P43 Me Cl CF₃ CMe₂ — — cyclopropyl 248-249° C. P44 Me Cl CF₃C(CH₂CH₂) — — C(Me)-(CH₂CH₂) MS (ES+) 552/554 (M + H)⁺ P45 Me 2-pyridylCF₃ CH₂ — — cyclopropyl 220-221° C. P46 Me Cl OCH₂CF₃ CH₂ — —cyclopropyl 174-176° C. P47 Me 2-pyridyl CF₃ C(CH₂CH₂) — — cyclopropyl224-225° C. P48 Me Cl OCH₂CF₃ C(CH₂CH₂) — — cyclopropyl 168-170° C. P49Me 3-pyridyl CF₃ CH₂ — — cyclopropyl 214-215° C. P50 Me Cl Cl C(CH₂CH₂)— — cyclopropyl 222-225° C. P51 Me Cl Br C(CH₂CH₂) — — cyclopropyl229-232° C. P52 Me NH₂ CF₃ C(CH₂CH₂) — — cyclopropyl 252-254° C. P53 MeNH₂ CF₃ CH₂ — — cyclopropyl 232-234° C. P54 Me I OCH₂CF₃ C(CH₂CH₂) — —cyclopropyl 235-236° C. P55 Me Br CF₃ CH₂ — — cyclopropyl 180-185° C.P56 Me Br Cl CH₂ — — cyclopropyl 215-224° C. P57 Me Br CF₃ C(CH₂CH₂) — —cyclopropyl 135-139° C. P58 Me Br Br CH₂ — — cyclopropyl 220-225° C. P59Me Br Cl C(CH₂CH₂) — — cyclopropyl 178-182° C. P60 Me NO₂ CF₃ CH₂cyclopropyl 195-199° C. P61 Me NO₂ CF₃ C(CH₂CH₂) cyclopropyl 215-217° C.P62 Me NO₂ Br C(CH₂CH₂) cyclopropyl 209-215° C. P63 Me NO₂ Cl C(CH₂CH₂)cyclopropyl 213-216° C. P64 Me NO₂ OCH₂CF₃ C(CH₂CH₂) cyclopropyl218-221° C. P65 Me Cl CF₃ CH₂ — — cyclobutyl MS (ES+) 526 (MH⁺) MS (ES−)524 (M − H)⁻ P66 Me Cl CF₃ CHMe — — cyclobutyl MS (ES+) 540 (MH⁺) MS(ES−) 538 (M − H)⁻ P67 Me Cl CF₃ CH(CH₂)C — — C(CH₂)₂ 157-163° C. P68 MeCl CF₃ CH(CH₂)C — — C(CH₂)₃ 143-145° C.

TABLE P′ Compounds of formula Ia′: (Ia′)

Cpd No. R₉₁ R₉₂ R₉₃ A X Y B Phys. Data P69 Me Cl OCH₂CF₃ CH₂ — —cyclopropyl 174-181° C. P70 Me Cl OCH₂CF₃ C(CH₂CH₂) — — cyclopropyl150-154° C. P71 Me I OCH₂CF₃ C(CH₂CH₂) — — cyclopropyl 180-184° C. P72Me I OCH₂CF₃ CH₂ — — cyclopropyl 205-211° C.

The examples which follow are intended to illustrate the invention andshow preferred compounds of formula I. Me means the methyl group. Etmeans the ethyl group. tBu is tert.-butyl. If no definition forsubstituent X is given, then p is 0, if X is a substituent, then p is 1.If no definition for substituent Y is given, then q is 0, if Y is asubstituent, then q is 1.

TABLE A Compounds of formula Ia: (Ia)

Comp. No. R₉₁ R₉₂ R₉₃ A X Y B A.1.1 Me Br CF₃ CH₂ — — cyclo- propylA.1.2 Me Br CF₃ CHMe — — cyclo- propyl A.1.3 Me Br CF₃ CMe₂ — — cyclo-propyl A.1.4 Me Br CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.5 Me F CF₃ CH₂ —— cyclo- propyl A.1.6 Me F CF₃ CHMe — — cyclo- propyl A.1.7 Me F CF₃CMe₂ — — cyclo- propyl A.1.8 Me F CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.9Me I CF₃ CH₂ — — cyclo- propyl A.1.10 Me I CF₃ CHMe — — cyclo- propylA.1.11 Me I CF₃ CMe₂ — — cyclo- propyl A.1.12 Me I CF₃ C(CH₂CH₂) — —cyclo- propyl A.1.13 Cl Cl CF₃ CH₂ — — cyclo- propyl A.1.14 Cl Cl CF₃CHMe — — cyclo- propyl A.1.15 Cl Cl CF₃ CMe₂ — — cyclo- propyl A.1.16 ClCl CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.17 Cl Br CF₃ CH₂ — — cyclo-propyl A.1.18 Cl Br CF₃ CHMe — — cyclo- propyl A.1.19 Cl Br CF₃ CMe₂ — —cyclo- propyl A.1.20 Cl Br CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.21 Cl FCF₃ CH₂ — — cyclo- propyl A.1.22 Cl F CF₃ CHMe — — cyclo- propyl A.1.23Cl F CF₃ CMe₂ — — cyclo- propyl A.1.24 Cl F CF₃ C(CH₂CH₂) — — cyclo-propyl A.1.25 Cl I CF₃ CH₂ — — cyclo- propyl A.1.26 Cl I CF₃ CHMe — —cyclo- propyl A.1.27 Cl I CF₃ CMe₂ — — cyclo- propyl A.1.28 Cl I CF₃C(CH₂CH₂) — — cyclo- propyl A.1.29 Br Cl CF₃ CH₂ — — cyclo- propylA.1.30 Br Cl CF₃ CHMe — — cyclo- propyl A.1.31 Br Cl CF₃ CMe₂ — — cyclo-propyl A.1.32 Br Cl CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.33 Br Br CF CH₂— — cyclo- propyl A.1.34 Br Br CF₃ CHMe — — cyclo- propyl A.1.35 Br BrCF₃ CMe₂ — — cyclo- propyl A.1.36 Br Br CF₃ C(CH₂CH₂) — — cyclo- propylA.1.37 Br F CF₃ CH₂ — — cyclo- propyl A.1.38 Br F CF₃ CHMe — — cyclo-propyl A.1.39 Br F CF₃ CMe₂ — — cyclo- propyl A.1.40 Br F CF₃ C(CH₂CH₂)— — cyclo- propyl A.1.41 Br I CF₃ CH₂ — — cyclo- propyl A.1.42 Br I CF₃CHMe — — cyclo- propyl A.1.43 Br I CF₃ CMe₂ — — cyclo- propyl A.1.44 BrI CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.45 Me Cl Cl CH₂ — — cyclo- propylA.1.46 Me Cl Cl CHMe — — cyclo- propyl A.1.47 Me Cl Cl CMe₂ — — cyclo-propyl A.1.48 Me Cl Cl C(CH₂CH₂) — — cyclo- propyl A.1.49 Me Br Cl CH₂ —— cyclo- propyl A.1.50 Me Br Cl CHMe — — cyclo- propyl A.1.51 Me Br ClCMe₂ — — cyclo- propyl A.1.52 Me Br Cl C(CH₂CH₂) — — cyclo- propylA.1.53 Me F Cl CH₂ — — cyclo- propyl A.1.54 Me F Cl CHMe — — cyclo-propyl A.1.55 Me F Cl CMe₂ — — cyclo- propyl A.1.56 Me F Cl C(CH₂CH₂) —— cyclo- propyl A.1.57 Me I Cl CH₂ — — cyclo- propyl A.1.58 Me I Cl CHMe— — cyclo- propyl A.1.59 Me I Cl CMe₂ — — cyclo- propyl A.1.60 Me I ClC(CH₂CH₂) — — cyclo- propyl A.1.61 Cl Cl Cl CH₂ — — cyclo- propyl A.1.62Cl Cl Cl CHMe — — cyclo- propyl A.1.63 Cl Cl Cl CMe₂ — — cyclo- propylA.1.64 Cl Cl Cl C(CH₂CH₂) — — cyclo- propyl A.1.65 Cl Br Cl CH₂ — —cyclo- propyl A.1.66 Cl Br Cl CHMe — — cyclo- propyl A.1.67 Cl Br ClCMe₂ — — cyclo- propyl A.1.68 Cl Br Cl C(CH₂CH₂) — — cyclo- propylA.1.69 Cl F Cl CH — — cyclo- propyl A.1.70 Cl F Cl CHMe — — cyclo-propyl A.1.71 Cl F Cl CMe₂ — — cyclo- propyl A.1.72 Cl F Cl C(CH₂CH₂) —— cyclo- propyl A.1.73 Cl I Cl CH₂ — — cyclo- propyl A.1.74 Cl I Cl CHMe— — cyclo- propyl A.1.75 Cl I Cl CMe₂ — — cyclo- propyl A.1.76 Cl I ClC(CH₂CH₂) — — cyclo- propyl A.1.77 Br Cl Cl CH₂ — — cyclo- propyl A.1.78Br Cl Cl CHMe — — cyclo- propyl A.1.79 Br Cl Cl CMe₂ — — cyclo- propylA.1.80 Br Cl Cl C(CH₂CH₂) — — cyclo- propyl A.1.81 Br Br Cl CH₂ — —cyclo- propyl A.1.82 Br Br Cl CHMe — — cyclo- propyl A.1.83 Br Br ClCMe₂ — — cyclo- propyl A.1.84 Br Br Cl C(CH₂CH₂) — — cyclo- propylA.1.85 Br F Cl CH₂ — — cyclo- propyl A.1.86 Br F Cl CHMe — — cyclo-propyl A.1.87 Br F Cl CMe₂ — — cyclo- propyl A.1.88 Br F Cl C(CH₂CH₂) —— cyclo- propyl A.1.89 Br I Cl CH₂ — — cyclo- propyl A.1.90 Br I Cl CHMe— — cyclo- propyl A.1.91 Br I Cl CMe₂ — — cyclo- propyl A.1.92 Br I ClC(CH₂CH₂) — — cyclo- propyl A.1.93 Me Cl Br CH₂ — — cyclo- propyl A.1.94Me Cl Br CHMe — — cyclo- propyl A.1.95 Me Cl Br CMe₂ — — cyclo- propylA.1.96 Me Cl Br C(CH₂CH₂) — — cyclo- propyl A.1.97 Me Br Br CH₂ — —cyclo- propyl A.1.98 Me Br Br CHMe — — cyclo- propyl A.1.99 Me Br BrCMe₂ — — cyclo- propyl A.1.100 Me Br Br C(CH₂CH₂) — — cyclo- propylA.1.101 Me F Br CH₂ — — cyclo- propyl A.1.102 Me F Br CHMe — — cyclo-propyl A.1.103 Me F Br CMe₂ — — cyclo- propyl A.1.104 Me F Br C(CH₂CH₂)— — cyclo- propyl A.1.105 Me I Br CH₂ — — cyclo- propyl A.1.106 Me I BrCHMe — — cyclo- propyl A.1.107 Me I Br CMe₂ — — cyclo- propyl A.1.108 MeI Br C(CH₂CH₂) — — cyclo- propyl A.1.109 Cl Cl Br CH₂ — — cyclo- propylA.1.110 Cl Cl Br CHMe — — cyclo- propyl A.1.111 Cl Cl Br CMe₂ — — cyclo-propyl A.1.112 Cl Cl Br C(CH₂CH₂) — — cyclo- propyl A.1.113 Cl Br Br CH₂— — cyclo- propyl A.1.114 Cl Br Br CHMe — — cyclo- propyl A.1.115 Cl BrBr CMe₂ — — cyclo- propyl A.1.116 Cl Br Br C(CH₂CH₂) — — cyclo- propylA.1.117 Cl F Br CH₂ — — cyclo- propyl A.1.118 Cl F Br CHMe — — cyclo-propyl A.1.119 Cl F Br CMe₂ — — cyclo- propyl A.1.120 Cl F Br C(CH₂CH₂)— — cyclo- propyl A.1.121 Cl I Br CH₂ — — cyclo- propyl A.1.122 Cl I BrCHMe — — cyclo- propyl A.1.123 Cl I Br CMe₂ — — cyclo- propyl A.1.124 ClI Br C(CH₂CH₂) — — cyclo- propyl A.1.125 Br Cl Br CH₂ — — cyclo- propylA.1.126 Br Cl Br CHMe — — cyclo- propyl A.1.127 Br Cl Br CMe₂ — — cyclo-propyl A.1.128 Br Cl Br C(CH₂CH₂) — — cyclo- propyl A.1.129 Br Br Br CH₂— — cyclo- propyl A.1.130 Br Br Br CHMe — — cyclo- propyl A.1.131 Br BrBr CMe₂ — — cyclo- propyl A.1.132 Br Br Br C(CH₂CH₂) — — cyclo- propylA.1.133 Br F Br CH₂ — — cyclo- propyl A.1.134 Br F Br CHMe — — cyclo-propyl A.1.135 Br F Br CMe₂ — — cyclo- propyl A.1.136 Br F Br C(CH₂CH₂)— — cyclo- propyl A.1.137 Br I Br CH₂ — — cyclo- propyl A.1.138 Br I BrCHMe — — cyclo- propyl A.1.139 Br I Br CMe₂ — — cyclo- propyl A.1.140 BrI Br C(CH₂CH₂) — — cyclo- propyl A.1.141 Me Cl OCHF₂ CH₂ — — cyclo-propyl A.1.142 Me Cl OCHF₂ CHMe — — cyclo- propyl A.1.143 Me Cl OCHF₂CMe₂ — — cyclo- propyl A.1.144 Me Cl OCHF₂ C(CH₂CH₂) — — cyclo- propylA.1.145 Me Br OCHF₂ CH₂ — — cyclo- propyl A.1.146 Me Br OCHF₂ CHMe — —cyclo- propyl A.1.147 Me Br OCHF₂ CMe₂ — — cyclo- propyl A.1.148 Me BrOCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.149 Me F OCHF₂ CH₂ — — cyclo-propyl A.1.150 Me F OCHF₂ CHMe — — cyclo- propyl A.1.151 Me F OCHF₂ CMe₂— — cyclo- propyl A.1.152 Me F OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.153Me I OCHF₂ CH₂ — — cyclo- propyl A.1.154 Me I OCHF₂ CHMe — — cyclo-propyl A.1.155 Me I OCHF₂ CMe₂ — — cyclo- propyl A.1.156 Me I OCHF₂C(CH₂CH₂) — — cyclo propyl A.1.157 Cl Cl OCHF₂ CH₂ — — cyclo- propylA.1.158 Cl Cl OCHF₂ CHMe — — cyclo- propyl A.1.159 Cl Cl OCHF₂ CMe₂ — —cyclo- propyl A.1.160 Cl Cl OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.161 ClBr OCHF₂ CH₂ — — cyclo- propyl A.1.162 Cl Br OCHF₂ CHMe — — cyclo-propyl A.1.163 Cl Br OCHF₂ CMe₂ — — cyclo- propyl A.1.164 Cl Br OCHF₂C(CH₂CH₂) — — cyclo- propyl A.1.165 Cl F OCHF₂ CH₂ — — cyclo- propylA.1.166 Cl F OCHF₂ CHMe — — cyclo- propyl A.1.167 Cl F OCHF₂ CMe₂ — —cyclo- propyl A.1.168 Cl F OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.169 ClI OCHF₂ CH₂ — — cyclo- propyl A.1.170 Cl I OCHF₂ CHMe — — cyclo- propylA.1.171 Cl I OCHF₂ CMe₂ — — cyclo- propyl A.1.172 Cl I OCHF₂ C(CH₂CH₂) —— cyclo- propyl A.1.173 Br Cl OCHF₂ CH₂ — — cyclo- propyl A.1.174 Br ClOCHF₂ CHMe — — cyclo- propyl A.1.175 Br Cl OCHF₂ CMe₂ — — cyclo- propylA.1.176 Br Cl OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.177 Br Br OCHF₂ CH₂— — cyclo- propyl A.1.178 Br Br OCHF₂ CHMe — — cyclo- propyl A.1.179 BrBr OCHF₂ CMe₂ — — cyclo- propyl A.1.180 Br Br OCHF₂ C(CH₂CH₂) — — cyclo-propyl A.1.181 Br F OCHF₂ CH₂ — — cyclo- propyl A.1.182 Br F OCHF₂ CHMe— — cyclo- propyl A.1.183 Br F OCHF₂ CMe₂ — — cyclo- propyl A.1.184 Br FOCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.185 Br I OCHF₂ CH₂ — — cyclo-propyl A.1.186 Br I OCHF₂ CHMe — — cyclo- propyl A.1.187 Br I OCHF₂ CMe₂— — cyclo- propyl A.1.188 Br I OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.189Me Cl OCH₂CF₃ CH₂ — — cyclo- propyl A.1.190 Me Cl OCH₂CF₃ CHMe — —cyclo- propyl A.1.191 Me Cl OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.192 Me ClOCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.193 Me Br OCH₂CF₃ CH₂ — — cyclo-propyl A.1.194 Me Br OCH₂CF₃ CHMe — — cyclo- propyl A.1.195 Me BrOCH₂CF₃ CMe₂ — — cyclo- propyl A.1.196 Me Br OCH₂CF₃ C(CH₂CH₂) — —cyclo- propyl A.1.197 Me F OCH₂CF₃ CH₂ — — cyclo- propyl A.1.198 Me FOCH₂CF₃ CHMe — — cyclo- propyl A.1.199 Me F OCH₂CF₃ CMe₂ — — cyclo-propyl A.1.200 Me F OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.201 Me IOCH₂CF₃ CH₂ — — cyclo- propyl A.1.202 Me I OCH₂CF₃ CHMe — — cyclo-propyl A.1.203 Me I OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.204 Me I OCH₂CF₃C(CH₂CH₂) — — cyclo- propyl A.1.205 Cl Cl OCH₂CF₃ CH₂ — — cyclo- propylA.1.206 Cl Cl OCH₂CF₃ CHMe — — cyclo- propyl A.1.207 Cl Cl OCH₂CF₃ CMe₂— — cyclo- propyl A.1.208 Cl Cl OCH₂CF₃ C(CH₂CH₂) — — cyclo- propylA.1.209 Cl Br OCH₂CF₃ CH₂ — — cyclo- propyl A.1.210 Cl Br OCH₂CF₃ CHMe —— cyclo- propyl A.1.211 Cl Br OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.212 ClBr OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.213 Cl F OCH₂CF₃ CH₂ — —cyclo- propyl A.1.214 Cl F OCH₂CF₃ CHMe — — cyclo- propyl A.1.215 Cl FOCH₂CF₃ CMe₂ — — cyclo- propyl A.1.216 Cl F OCH₂CF₃ C(CH₂CH₂) — — cyclo-propyl A.1.217 Cl I OCH₂CF₃ CH₂ — — cyclo- propyl A.1.218 Cl I OCH₂CF₃CHMe — — cyclo- propyl A.1.219 Cl I OCH₂CF₃ CMe₂ — — cyclo- propylA.1.220 Cl I OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.221 Br Cl OCH₂CF₃CH₂ — — cyclo- propyl A.1.222 Br Cl OCH₂CF₃ CHMe — — cyclo- propylA.1.223 Br Cl OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.224 Br Cl OCH₂CF₃C(CH₂CH₂) — — cyclo- propyl A.1.225 Br Br OCH₂CF₃ CH₂ — — cyclo- propylA.1.226 Br Br OCH₂CF₃ CHMe — — cyclo- propyl A.1.227 Br Br OCH₂CF₃ CMe₂— — cyclo- propyl A.1.228 Br Br OCH₂CF₃ C(CH₂CH₂) — — cyclo- propylA.1.229 Br F OCH₂CF₃ CH₂ — — cyclo- propyl A.1.230 Br F OCH₂CF₃ CHMe — —cyclo- propyl A.1.231 Br F OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.232 Br FOCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.233 Br I OCH₂CF₃ CH₂ — — cyclo-propyl A.1.234 Br I OCH₂CF₃ CHMe — — cyclo- propyl A.1.235 Br I OCH₂CF₃CMe₂ — — cyclo- propyl A.1.236 Br I OCH₂CF₃ C(CH₂CH₂) — — cyclo- propylA.1.237 Me Cl CHF₂ CH₂ — — cyclo- propyl A.1.238 Me Cl CHF₂ CHMe — —cyclo- propyl A.1.239 Me Cl CHF₂ CMe₂ — — cyclo- propyl A.1.240 Me ClCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.241 Me Br CHF₂ CH₂ — — cyclo-propyl A.1.242 Me Br CHF₂ CHMe — — cyclo- propyl A.1.243 Me Br CHF₂ CMe₂— — cyclo- propyl A.1.244 Me Br CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.245Me F CHF₂ CH — — cyclo- propyl A.1.246 Me F CHF₂ CHMe — — cyclo- propylA.1.247 Me F CHF₂ CMe₂ — — cyclo- propyl A.1.248 Me F CHF₂ C(CH₂CH₂) — —cyclo- propyl A.1.249 Me I CHF₂ CH₂ — — cyclo- propyl A.1.250 Me I CHF₂CHMe — — cyclo- propyl A.1.251 Me I CHF₂ CMe₂ — — cyclo- propyl A.1.252Me I CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.253 Cl Cl CHF₂ CH₂ — — cyclo-propyl A.1.254 Cl Cl CHF₂ CHMe — — cyclo- propyl A.1.255 Cl Cl CHF₂ CMe₂— — cyclo- propyl A.1.256 Cl Cl CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.257Cl Br CHF₂ CH₂ — — cyclo- propyl A.1.258 Cl Br CHF₂ CHMe — — cyclo-propyl A.1.259 Cl Br CHF₂ CMe₂ — — cyclo- propyl A.1.260 Cl Br CHF₂C(CH₂CH₂) — — cyclo- propyl A.1.261 Cl F CHF₂ CH₂ — — cyclo- propylA.1.262 Cl F CHF₂ CHMe — — cyclo- propyl A.1.263 Cl F CHF₂ CMe₂ — —cyclo- propyl A.1.264 Cl F CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.265 Cl ICHF₂ CH₂ — — cyclo- propyl A.1.266 Cl I CHF₂ CHMe — — cyclo- propylA.1.267 Cl I CHF₂ CMe₂ — — cyclo- propyl A.1.268 Cl I CHF₂ C(CH₂CH₂) — —cyclo- propyl A.1.269 Br Cl CHF₂ CH₂ — — cyclo- propyl A.1.270 Br ClCHF₂ CHMe — — cyclo- propyl A.1.271 Br Cl CHF₂ CMe₂ — — cyclo- propylA.1.272 Br Cl CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.273 Br Br CHF₂ CH₂ —— cyclo- propyl A.1.274 Br Br CHF₂ CHMe — — cyclo- propyl A.1.275 Br BrCHF₂ CMe₂ — — cyclo- propyl A.1.276 Br Br CHF₂ C(CH₂CH₂) — — cyclo-propyl A.1.277 Br F CHF₂ CH₂ — — cyclo- propyl A.1.278 Br F CHF₂ CHMe —— cyclo- propyl A.1.279 Br F CHF₂ CMe — — cyclo- propyl A.1.280 Br FCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.281 Br I CHF₂ CH₂ — — cyclo- propylA.1.282 Br I CHF₂ CHMe — — cyclo- propyl A.1.283 Br I CHF₂ CMe₂ — —cyclo- propyl A.1.284 Br I CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.285 MeCl CH₂CF₃ CH₂ — — cyclo- propyl A.1.286 Me Cl CH₂CF₃ CHMe — — cyclo-propyl A.1.287 Me Cl CH₂CF₃ CMe₂ — — cyclo- propyl A.1.288 Me Cl CH₂CF₃C(CH₂CH₂) — — cyclo- propyl A.1.289 Me Br CH₂CF₃ CH₂ — — cyclo- propylA.1.290 Me Br CH₂CF₃ CHMe — — cyclo- propyl A.1.291 Me Br CH₂CF₃ CMe₂ —— cyclo- propyl A.1.292 Me Br CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.293Me F CH₂CF₃ CH₂ — — cyclo- propyl A.1.294 Me F CH₂CF₃ CHMe — — cyclo-propyl A.1.295 Me F CH₂CF₃ CMe₂ — — cyclo- propyl A.1.296 Me F CH₂CF₃C(CH₂CH₂) — — cyclo- propyl A.1.297 Me I CH₂CF₃ CH₂ — — cyclo- propylA.1.298 Me I CH₂CF₃ CHMe — — cyclo- propyl A.1.299 Me I CH₂CF₃ CMe₂ — —cyclo- propyl A.1.300 Me I CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.301 ClCl CH₂CF₃ CH₂ — — cyclo- propyl A.1.302 Cl Cl CH₂CF₃ CHMe — — cyclo-propyl A.1.303 Cl Cl CH₂CF₃ CMe₂ — — cyclo- propyl A.1.304 Cl Cl CH₂CF₃C(CH₂CH₂) — — cyclo- propyl A.1.305 Cl Br CH₂CF₃ CH₂ — — cyclo- propylA.1.306 Cl Br CH₂CF₃ CHMe — — cyclo- propyl A.1.307 Cl Br CH₂CF₃ CMe₂ —— cyclo- propyl A.1.308 Cl Br CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.309Cl F CH₂CF₃ CH₂ — — cyclo- propyl A.1.310 Cl F CH₂CF₃ CHMe — — cyclo-propyl A.1.311 Cl F CH₂CF₃ CMe₂ — — cyclo- propyl A.1.312 Cl F CH₂CF₃C(CH₂CH₂) — — cyclo- propyl A.1.313 Cl I CH₂CF₃ CH₂ — — cyclo- propylA.1.314 Cl I CH₂CF₃ CHMe — — cyclo- propyl A.1.315 Cl I CH₂CF₃ CMe₂ — —cyclo- propyl A.1.316 Cl I CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.317 BrCl CH₂CF₃ CH₂ — — cyclo- propyl A.1.318 Br Cl CH₂CF₃ CHMe — — cyclo-propyl A.1.319 Br Cl CH₂CF₃ CMe₂ — — cyclo- propyl A.1.320 Br Cl CH₂CF₃C(CH₂CH₂) — — cyclo- propyl A.1.321 Br Br CH₂CF₃ CH₂ — — cyclo- propylA.1.322 Br Br CH₂CF₃ CHMe — — cyclo- propyl A.1.323 Br Br CH₂CF₃ CMe₂ —— cyclo- propyl A.1.324 Br Br CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.325Br F CH₂CF₃ CH₂ — — cyclo- propyl A.1.326 Br F CH₂CF₃ CHMe — — cyclo-propyl A.1.327 Br F CH₂CF₃ CMe₂ — — cyclo- propyl A.1.328 Br F CH₂CF₃C(CH₂CH₂) — — cyclo- propyl A.1.329 Br I CH₂CF₃ CH₂ — — cycJo- propylA.1.330 Br I CH₂CF₃ CHMe — — cyclo- propyl A.1.331 Br I CH₂CF₃ CMe₂ — —cyclo- propyl A.1.332 Br I CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.333 MeCl CF₃ CH₂ — — cyclo- propyl A.1.334 Me Cl CF₃ CHMe — — cyclo- propylA.1.335 Me Cl CF₃ CHCF₃ — — cyclo- propyl A.1.336 Me Cl CF₃ CHEt — —cyclo- propyl A.1.337 Me Cl CF₃ CH(cyclo- — — cyclo- propyl) propylA.1.338 Me Cl CF₃ CHnPr — — cyclo- propyl A.1.339 Me Cl CF₃ CHtBu — —cyclo- propyl A.1.340 Me Cl CF₃ CH(CH═CH₂) — — cyclo- propyl A.1.341 MeCl CF₃ CH(CH═CH- — — cyclo- Me) propyl A.1.342 Me Cl CF₃ CH(CMe═CH₂) — —cyclo- propyl A.1.343 Me Cl CF₃ CH(CH₂CH═CH₂) — — cyclo- propyl A.1.344Me Cl CF₃ CH(C═CH) — — cyclo- propyl A.1.345 Me Cl CF₃ CMe₂ — — cyclo-propyl A.1.346 Me Cl CF₃ CHCN — — cyclo- propyl A.1.347 Me Cl CF₃CH(CH₂SMe) — — cyclo- propyl A.1.348 Me Cl CF₃ CH(CH₂S(O)₂Me) — — cyclo-propyl A.1.349 Me Cl CF₃ CH(CH₂OMe) — — cyclo- propyl A.1.350 Me Cl CF₃CH(CH₂Cl) — — cyclo- propyl A.1.351 Me Cl CF₃ C(CH₂CH₂) — — cyclo-propyl A.1.352 Me Cl CF₃ C(CH₂CHF) — — cyclo- propyl A.1.353 Me Cl CF₃C(CH₂CF₂) — — cyclo- propyl A.1.354 Me Cl CF₃ C(CH₂CHCl) — — cyclo-propyl A.1.355 Me Cl CF₃ C(CH₂CFCl) — — cyclo- propyl A.1.356 Me Cl CF₃C(CH₂CCl₂) — — cyclo- propyl A.1.357 Me Cl CF₃ C(CH₂CHBr) — — cyclo-propyl A.1.358 Me Cl CF₃ C(CH₂CBr₂) — — cyclo- propyl A.1.359 Me Cl CF₃C(CH₂CHMe) — — cyclo- propyl A.1.360 Me Cl CF₃ C(CH₂CMe₂) — — cyclo-propyl A.1.361 Me Cl CF₃ C(CH₂CHEt) — — cyclo- propyl A.1.362 Me Cl CF₃C(CH₂CEt₂) — — cyclo- propyl A.1.363 Me Cl CF₃ CH₂CH₂ — — cyclo- propylA.1.364 Me Cl CF₃ CH═CH — — cyclo- propyl A.1.365 Me Cl CF₃ CHMeCH₂ — —cyclo- propyl A.1.366 Me Cl CF₃ C(CH₂OCH₂) — — cyclo- propyl A.1.367 MeCl CF₃ C(CH₂S(O)₂—CH₂) — — cyclo- propyl A.1.368 Me Cl CF₃ CH₂ O —cyclo- propyl A.1.369 Me Cl CF₃ CHMe O — cyclo- propyl A.1.370 Me Cl CF₃CMe₂ O — cyclo- propyl A.1.371 Me Cl CF₃ C(CH₂CH₂) O — cyclo- propylA.1.372 Me Cl CF₃ CHMe N-iso- — cyclo- propyl propyl A.1.373 Me Cl CF₃CMe₂ N-iso- — cyclo- butyl propyl A.1.374 Me Cl CF₃ CH₂ NH — cyclo-propyl A.1.375 Me Cl CF₃ CHMe NMe — cyclo- propyl A.1.376 Me Cl CF₃ CMe₂NEt — cyclo- propyl A.1.377 Me Cl CF₃ CH₂ O CH₂ cyclo- propyl A.1.378 MeCl CF₃ CHMe O CH₂ cyclo- propyl A.1.379 Me Cl CF₃ CMe₂ O CH₂ cyclo-propyl A.1.380 Me Cl CF₃ C(CH₂CH₂) O CH₂ cyclo- propyl A.1.381 Me Cl CF₃CHMe S(O) CH₂ cyclo- propyl A.1.382 Me Cl CF₃ CMe₂ S(O)₂ CH₂ cyclo-propyl A.1.383 Me Cl CF₃ CH₂ NH CH₂ cyclo- propyl A.1.384 Me Cl CF₃ CHMeNMe CH₂ cyclo- propyl A.1.385 Me Cl CF₃ CMe₂ NEt CH₂ cyclo- propylA.1.386 Me Cl CF₃ CH₂ O CHMe cyclo- propyl A.1.387 Me Cl CF₃ CH₂ O CHCF₃cyclo- propyl A.1.388 Me Cl CF₃ CH₂ O CHEt cyclo- propyl A.1.389 Me ClCF₃ CH₂ O CH-(cyclo- cyclo- propyl) propyl A.1.390 Me Cl CF₃ CH₂ O CHnPrcyclo- propyl A.1.391 Me Cl CF₃ CH₂ O CHtBu cyclo- propyl A.1.392 Me ClCF₃ CH₂ O CH(CH═CH₂) cyclo- propyl A.1.393 Me Cl CF₃ CH₂ O CH(CH═CHMe)cyclo- propyl A.1.394 Me Cl CF₃ CH₂ O CH—(CMe═CH₂) cyclo- propyl A.1.395Me Cl CF₃ CH₂ O CH(CH₂CH═CH₂) cyclo- propyl A.1.396 Me Cl CF₃ CH₂ OCH(C═CH) cyclo- propyl A.1.397 Me Cl CF₃ CH₂ O CMe₂ cyclo- propylA.1.398 Me Cl CF₃ CH₂ O CHCN cyclo- propyl A.1.399 Me Ci CF₃ CH₂ OCH(CH₂S-Me) cyclo- propyl A.1.400 Me Cl CF₃ CH₂ O CH(CH₂S—(O)₂Me) cyclo-propyl A.1.401 Me Cl CF₃ CH₂ O CH(CH₂O-Me) cyclo- propyl A.1.402 Me ClCF₃ CH₂ O CH(CH₂Cl) cyclo- propyl A.1.403 Me Cl CF₃ CH₂ O C(CH₂CH₂)cyclo- propyl A.1.404 Me Cl CF₃ CH₂ O C(CH₂CHF) cyclo- propyl A.1.405 MeCl CF₃ CH₂ O C(CH₂CF₂) cyclo- propyl A.1.406 Me Cl CF₃ CH₂ O C(CH₂CHCl)cyclo- propyl A.1.407 Me Cl CF₃ CH₂ O C(CH₂CFCl) cyclo- propyl A.1.408Me Cl CF₃ CH₂ O C(CH₂CCl₂) cyclo- propyl A.1.409 Me Cl CF₃ CH₂ OC(CH₂CHBr) cyclo- propyl A.1.410 Me Cl CF₃ CH₂ O C(CH₂CBr₂) cyclo-propyl A.1.411 Me Cl CF₃ CH₂ O C(CH₂CHMe) cyclo- propyl A.1.412 Me ClCF₃ CH₂ O C(CH₂CMe₂) cyclo- propyl A.1.413 Me Cl CF₃ CH₂ O C(CH₂CHEt)cyclo- propyl A.1.414 Me Cl CF₃ CH₂ O C(CH₂C-Et₂) cyclo- propyl A.1.415Me Cl CF₃ CH₂ O CH₂CH₂ cyclo- propyl A.1.416 Me Cl CF₃ CH₂ O CH═CHcyclo- propyl A.1.417 Me Cl CF₃ CH₂ O CHMeCH₂ cyclo- propyl A.1.418 MeCl CF₃ CH₂ — — 1-fluoro- cyclo- propyl A.1.419 Me Cl CF₃ CH₂ — —1-chloro- cyclo- propyl A.1.420 Me Cl CF₃ CH₂ — — 1-bromo- cyclo- propylA.1.421 Me Cl CF₃ CH₂ — — 1-methyl- cyclo- propyl A.1.422 Me Cl CF₃ CH₂— — 1-ethyl- cyclo- propyl A.1.423 Me Cl CF₃ CH₂ — — 1-cyano- cyclo-propyl A.1.424 Me Cl CF₃ CH₂ — — 1-methyl- thiocyclo- propyl A.1.425 MeCl CF₃ CH₂ — — 1- methoxy- cyclo- propyl A.1.426 Me Cl CF₃ CH₂ — —1-hydroxy- cyclo- propyl A.1.427 Me Cl CF₃ CH₂ — — 1-trifluoro- methyl-cyclo- propyl A.1.428 Me Cl CF₃ CH₂ — — 2-fluoro- cyclo- propyl A.1.429Me Cl CF₃ CH₂ — — 2,2- difluoro- cyclo- propyl A.1.430 Me Cl CF₃ CH₂ — —2-chloro- cyclo- propyl A.1.431 Me Cl CF₃ CH₂ — — 2,2- dichloro- cyclo-propyl A.1.432 Me Cl CF₃ CH₂ — — 2-bromo- cyclo- propyl A.1.433 Me ClCF₃ CH₂ — — 2,2- dibromo- cyclo- propyl A.1.434 Me Cl CF₃ CH₂ — —2-chloro- 2-fluoro- cyclo- propyl A.1.435 Me Cl CF₃ CH₂ — — 2-methyl-cyclo- propyl A.1.436 Me Cl CF₃ CH₂ — — 2,2- dimethyl- cyclo- propylA.1.437 Me Cl CF₃ CH₂ — — 2-ethyl- cyclo- propyl A.1.438 Me Cl CF₃ CH₂ —— 2,2- diethyl- cyclo- propyl A.1.439 Me Cl CF₃ CH₂ — — 2- cyanocyclo-propyl A.1.440 Me Cl CF₃ CH₂ — — 2-methyl- thiocyclo- propyl A.1.441 MeCl CF₃ CH₂ — — 2- methoxy- cyclo- propyl A.1.442 Me Cl CF₃ CH₂ — —2-hydroxy- cyclo- propyl A.1.443 Me Cl CF₃ CH₂ — — 2-trifluoro- methyl-cyclo- propyl A.1.444 Me Cl CF₃ CH₂ — — cyclo-butyl A.1.445 Me Cl CF₃CH₂ — — 2-fluoro- cyclo-butyl A.1.446 Me Cl CF₃ CH₂ — — 2,2- difluoro-cyclo-butyl A.1.447 Me Cl CF₃ CH₂ — — 2-chloro- cyclo-butyl A.1.448 MeCl CF₃ CH₂ — — 2,2- dichloro- cyclo-butyl A.1.449 Me Cl CF₃ CH₂ — —2-bromo- cyclo-butyl A.1.450 Me Cl CF₃ CH₂ — — 2,2- dibromo- cyclo-butylA.1.451 Me Cl CF₃ CH₂ — — 2-chloro- 2-fluoro- cyclo-butyl A.1.452 Me ClCF₃ CH₂ — — 2-methyl- cyclo-butyl A.1.453 Me Cl CF₃ CH₂ — — 2,2-dimethyl- cyclo-butyl A.1.454 Me Cl CF₃ CH₂ — — 2-ethyl- cyclo-butylA.1.455 Me Cl CF₃ CH₂ — — 2,2- diethyl- cyclo-butyl A.1.456 Me Cl CF₃CH₂ — — 2-cyano- cyclo-butyl A.1.457 Me Cl CF₃ CH₂ — — 2-methyl-thiocyclo- butyl A.1.458 Me Cl CF₃ CH₂ — — 2- methoxy- cyclo-butylA.1.459 Me Cl CF₃ CH₂ — — 2-hydroxy- cyclo-butyl A.1.460 Me Cl CF₃ CH₂ —— 2-trifluoro- methyl- cyclo-butyl A.1.461 Me Cl CF₃ CH₂ — — 3-methyl-cyclo-butyl A.1.462 Me Cl CF₃ CH₂ — — 3,3- dimethyl- cyclo-butyl A.1.463Me Cl CF₃ CH₂ — — 3-chloro- cyclo-butyl A.1.464 Me Cl CF₃ CH₂ — — 3,3-dichloro- cyclo-butyl A.1.465 Me Cl CF₃ CHMe — — 1-fluoro- cyclo- propylA.1.466 Me Cl CF₃ CHMe — — 1- chlorocyclo- propyl A.1.467 Me Cl CF₃ CHMe— — 1-bromo- cyclo- propyl A.1.468 Me Cl CF₃ CHMe — — 1-methyl- cyclo-propyl A.1.469 Me Cl CF₃ CHMe — — 1-ethyl- cyclo- propyl A.1.470 Me ClCF₃ CHMe — — 1-cyano- cyclo- propyl A.1.471 Me Cl CF₃ CHMe — — 1-methyl-thiocyclo- propyl A.1.472 Me Cl CF₃ CHMe — — 1- methoxy- cyclo- propylA.1.473 Me Cl CF₃ CHMe — — 1-hydroxy- cyclo- propyl A.1.474 Me Cl CF₃CHMe — — 1-trifluoro- methyl- cyclo- propyl A.1.475 Me Cl CF₃ CHMe — —2-fluoro- cyclo- propyl A.1.476 Me Cl CF₃ CHMe — — 2,2- difluoro- cyclo-propyl A.1.477 Me Cl CF₃ CHMe — — 2-chloro- cyclo- propyl A.1.478 Me ClCF₃ CHMe — — 2,2- dichloro- cyclo- propyl A.1.479 Me Cl CF₃ CHMe — —2-bromo- cyclo- propyl A.1.480 Me Cl CF₃ CHMe — — 2,2- dibromo- cyclo-propyl A.1.481 Me Cl CF₃ CHMe — — 2-chloro- 2-fluoro- cyclo- propylA.1.482 Me Cl CF₃ CHMe — — 2-methyl- cyclo- propyl A.1.483 Me Cl CF₃CHMe — — 2,2- dimethyl- cyclo- propyl A.1.484 Me Cl CF₃ CHMe — —2-ethyl- cyclo- propyl A.1.485 Me Cl CF₃ CHMe — — 2,2- diethyl- cyclo-propyl A.1.486 Me Cl CF₃ CHMe — — 2-cyano- cyclo- pro pyl A.1.487 Me ClCF₃ CHMe — — 2-methyl- thiocyclo- propyl A.1.488 Me Cl CF₃ CHMe — — 2-methoxy- cyclo- propyl A.1.489 Me Cl CF₃ CHMe — — 2-hydroxy- cyclo-propyl A.1.490 Me Cl CF₃ CHMe — — 2-trifluoro- methyl- cyclo- propylA.1.491 Me Cl CF₃ CHMe — — cyclo-butyl A.1.492 Me Cl CF₃ CHMe — —2-fluoro- cyclo-butyl A.1.493 Me Cl CF₃ CHMe — — 2,2- difluoro-cyclo-butyl A.1.494 Me Cl CF₃ CHMe — — 2- chlorocyclo- butyl A.1.495 MeCl CF₃ CHMe — — 2,2- dichloro- cyclo-butyl A.1.496 Me Cl CF₃ CHMe — —2-bromo- cyclo-butyl A.1.497 Me Cl CF₃ CHMe — — 2,2- dibromo-cyclo-butyl A.1.498 Me Cl CF₃ CHMe — — 2-chloro- 2-fluoro- cyclo-butylA.1.499 Me Cl CF₃ CHMe — — 2-methyl- cyclo-butyl A.1.500 Me Cl CF₃ CHMe— — 2,2- dimethyl- cyclo-butyl A.1.501 Me Cl CF₃ CHMe — — 2-ethyl-cyclo-butyl A.1.502 Me Cl CF₃ CHMe — — 2,2- diethyl- cyclo-butyl A.1.503Me Cl CF₃ CHMe — — 2- cyanocyclo- butyl A.1.504 Me Cl CF₃ CHMe — —2-methyl- thiocyclo- butyl A.1.505 Me Cl CF₃ CHMe — — 2- methoxy-cyclo-butyl A.1.506 Me Cl CF₃ CHMe — — 2-hydroxy- cyclo-butyl A.1.507 MeCl CF₃ CHMe — — 2-trifluoro- methyl- cyclo-butyl A.1.508 Me Cl CF₃ CHMe— — 3-methyl- cyclo-butyl A.1.509 Me Cl CF₃ CHMe — — 3,3- dimethyl-cyclo-butyl A.1.510 Me Cl CF₃ CHMe — — 3-chloro- cyclo-butyl A.1.511 MeCl CF₃ CHMe — — 3,3- dichloro- cyclo-butyl A.1.512 Me Cl CF₃ CMe₂ — —1-fluoro- cyclo- propyl A.1.513 Me Cl CF₃ CMe₂ — — 1-chloro- cyclo-propyl A.1.514 Me Cl CF₃ CMe₂ — — 1-bromo- cyclo- propyl A.1.515 Me ClCF₃ CMe₂ — — 1-methyl- cyclo- propyl A.1.516 Me Cl CF₃ CMe₂ — — 1-ethyl-cyclo- propyl A.1.517 Me Cl CF₃ CMe₂ — — 1-cyano- cyclo- propyl A.1.518Me Cl CF₃ CMe₂ — — 1-methyl- thiocyclo- propyl A.1.519 Me Cl CF₃ CMe₂ —— 1- methoxy- cyclo- propyl A.1.520 Me Cl CF₃ CMe₂ — — 1-hydroxy- cyclo-propyl A.1.521 Me Cl CF₃ CMe₂ — — 1-trifluoro- methyl- cyclo- propylA.1.522 Me Cl CF₃ CMe₂ — — 2-fluoro- cyclo- propyl A.1.523 Me Cl CF₃CMe₂ — — 2,2- difluoro- cyclo- propyl A.1.524 Me Cl CF₃ CMe₂ — —2-chloro- cyclo- propyl A.1.525 Me Cl CF₃ CMe₂ — — 2,2- dichloro- cyclo-propyl A.1.526 Me Cl CF₃ CMe₂ — — 2-bromo- cyclo- propyl A.1.527 Me ClCF₃ CMe₂ — — 2,2- dibromo- cyclo- propyl A.1.528 Me Cl CF₃ CMe₂ — —2-chloro- 2-fluoro- cyclo- propyl A.1.529 Me Cl CF₃ CMe₂ — — 2-methyl-cyclo- propyl A.1.530 Me Cl CF₃ CMe₂ — — 2,2- dimethyl- cyclo- propylA.1.531 Me Cl CF₃ CMe₂ — — 2-ethyl- cyclo- propyl A.1.532 Me Cl CF₃ CMe₂— — 2,2- diethyl- cyclo- propyl A.1.533 Me Cl CF₃ CMe₂ — — 2-cyano-cyclo- propyl A.1.534 Me Cl CF₃ CMe₂ — — 2-methyl- thiocyclo- propylA.1.535 Me Cl CF₃ CMe₂ — — 2- methoxy- cyclo- propyl A.1.536 Me Cl CF₃CMe₂ — — 2-hydroxy- cyclo- propyl A.1.537 Me Cl CF₃ CMe₂ — —2-trifluoro- methyl- cyclo- propyl A.1.538 Me Cl CF₃ CMe₂ — —cyclo-butyl A.1.539 Me Cl CF₃ CMe₂ — — 2-fluoro- cyclo-butyl A.1.540 MeCl CF₃ CMe₂ — — 2,2- difluoro- cyclo-butyl A.1.541 Me Cl CF₃ CMe₂ — —2-chloro- cyclo-butyl A.1.542 Me Cl CF₃ CMe₂ — — 2,2- dichloro-cyclo-butyl A.1.543 Me Cl CF₃ CMe₂ — — 2-bromo- cyclo-butyl A.1.544 MeCl CF₃ CMe₂ — — 2,2- dibromo- cyclo-butyl A.1.545 Me Cl CF₃ CMe₂ — —2-chloro- 2-fluoro- cyclo-butyl A.1.546 Me Cl CF₃ CMe₂ — — 2-methyl-cyclo-butyl A.1.547 Me Cl CF₃ CMe₂ — — 2,2- dimethyl- cyclo-butylA.1.548 Me Cl CF₃ CMe₂ — — 2-ethyl- cyclo-butyl A.1.549 Me Cl CF₃ CMe₂ —— 2,2- diethyl- cyclo-butyl A.1.550 Me Cl CF₃ CMe₂ — — 2-cyano-cyclo-butyl A.1.551 Me Cl CF₃ CMe₂ — — 2-methyl- thiocyclo- butylA.1.552 Me Cl CF₃ CMe₂ — — 2- methoxy- cyclo-butyl A.1.553 Me Cl CF₃CMe₂ — — 2-hydroxy- cyclo-butyl A.1.554 Me Cl CF₃ CMe₂ — — 2-trifluoro-methyl- cyclo-butyl A.1.555 Me Cl CF₃ CMe₂ — — 3-methyl- cyclo-butylA.1.556 Me Cl CF₃ CMe₂ — — 3,3- dimethyl- cyclo-butyl A.1.557 Me Cl CF₃CMe₂ — — 3-chloro- cyclo-butyl A.1.558 Me Cl CF₃ CMe₂ — — 3,3- dichloro-cyclo-butyl A.1.559 Me Cl CF₃ CMe₂ — — 2-hydroxy- cyclo-butyl A.1.560 MeCl CF₃ CMe₂ — — 2-trifluoro- methyl- cyclo-butyl A.1.561 Me Cl CF₃ CMe₂— — 3-methyl- cyclo-butyl A.1.562 Me Cl CF₃ CMe₂ — — 3,3- dimethyl-cyclo-butyl A.1.563 Me Cl CF₃ CMe₂ — — 3-chloro- cyclo-butyl A.1.564 MeCl CF₃ CMe₂ — — 3,3- dichloro- cyclo-butyl A.1.565 Me Cl CF₃ C(CH₂CH₂) —— 1-fluoro- cyclo- propyl A.1.566 Me Cl CF₃ C(CH₂CH₂) — — 1-chloro-cyclo- propyl A.1.567 Me Cl CF₃ C(CH₂CH₂) — — 1-bromo- cyclo- propylA.1.568 Me Cl CF₃ C(CH₂CH₂) — — 1-methyl- cyclo- propyl A.1.569 Me ClCF₃ C(CH₂CH₂) — — 1-ethyl- cyclo- propyl A.1.570 Me Cl CF₃ C(CH₂CH₂) — —1-cyano- cyclo- propyl A.1.571 Me Cl CF₃ C(CH₂CH₂) — — 1-methyl-thiocyclo- propyl A.1.572 Me Cl CF₃ C(CH₂CH₂) — — 1- methoxy- cyclo-propyl A.1.573 Me Cl CF₃ C(CH₂CH₂) — — 1-hydroxy- cyclo- propyl A.1.574Me Cl CF₃ C(CH₂CH₂) — — 1-trifluoro- methyl- cyclo- propyl A.1.575 Me ClCF₃ C(CH₂CH₂) — — 2-fluoro- cyclo- propyl A.1.576 Me Cl CF₃ C(CH₂CH₂) —— 2,2- difluoro- cyclo- propyl A.1.577 Me Cl CF₃ C(CH₂CH₂) — — 2-chloro-cyclo- propyl A.1.578 Me Cl CF₃ C(CH₂CH₂) — — 2,2- dichloro- cyclo-propyl A.1.579 Me Cl CF₃ C(CH₂CH₂) — — 2-bromo- cyclo- propyl A.1.580 MeCl CF₃ C(CH₂CH₂) — — 2,2- dibromo- cyclo- propyl A.1.581 Me Cl CF₃C(CH₂CH₂) — — 2-chloro- 2-fluoro- cyclo- propyl A.1.582 Me Cl CF₃C(CH₂CH₂) — — 2-methyl- cyclo- propyl A.1.583 Me Cl CF₃ C(CH₂CH₂) — —2,2- dimethyl- cyclo- propyl A.1.584 Me Cl CF₃ C(CH₂CH₂) — — 2-ethyl-cyclo- propyl A.1.585 Me Cl CF₃ C(CH₂CH₂) — — 2,2- diethyl- cyclo-propyl A.1.586 Me Cl CF₃ C(CH₂CH₂) — — 2-cyano- cyclo- propyl A.1.587 MeCl CF₃ C(CH₂CH₂) — — 2-methyl- thiocyclo- propyl A.1.588 Me Cl CF₃C(CH₂CH₂) — — 2- methoxy- cyclo- propyl A.1.589 Me Cl CF₃ C(CH₂CH₂) — —2-hydroxy- cyclo- propyl A.1.590 Me Cl CF₃ C(CH₂CH₂) — — 2-trifluoro-methyl- cyclo- propyl A.1.591 Me Cl CF₃ C(CH₂CH₂) — — cyclo-butyl A1.592Me Cl CF₃ C(CH₂CH₂) — — 2-fluoro- cyclo-butyl A1.593 Me Cl CF₃ C(CH₂CH₂)— — 2,2- difluoro- cyclo-butyl A1.594 Me Cl CF₃ C(CH₂CH₂) — — 2-chloro-cyclo-butyl A1.595 Me Cl CF₃ C(CH₂CH₂) — — 2,2- dichloro- cyclo-butylA1.596 Me Cl CF₃ C(CH₂CH₂) — — 2-bromo- cyclo-butyl A1.597 Me Cl CF₃C(CH₂CH₂) — — 2,2- dibromo- cyclo-butyl A1.598 Me Cl CF₃ C(CH₂CH₂) — —2-chloro- 2-fluoro- cyclo-butyl A1.599 Me Cl CF₃ C(CH₂CH₂) — — 2-methyl-cyclo-butyl A1.600 Me Cl CF₃ C(CH₂CH₂) — — 2,2- dimethyl- cyclo-butylA1.601 Me Cl CF₃ C(CH₂CH₂) — — 2-ethyl- cyclo-butyl A1.602 Me Cl CF₃C(CH₂CH₂) — — 2,2- diethyl- cyclo-butyl A1.603 Me Cl CF₃ C(CH₂CH₂) — —2-cyano- cyclo-butyl A1.604 Me Cl CF₃ C(CH₂CH₂) — — 2-methyl- thiocyclo-butyl A1.605 Me Cl CF₃ C(CH₂CH₂) — — 2- methoxy- cyclo-butyl A1.606 MeCl CF₃ C(CH₂CH₂) — — 2-hydroxy- cyclo-butyl A1.607 Me Cl CF₃ C(CH₂CH₂) —— 2-trifluoro- methyl- cyclo-butyl A1.608 Me Cl CF₃ C(CH₂CH₂) — —3-methyl- cyclo-butyl A1.609 Me Cl CF₃ C(CH₂CH₂) — — 3,3- dimethyl-cyclo-butyl A1.610 Me Cl CF₃ C(CH₂CH₂) — — 3-chloro- cyclo-butyl A1.611Me Cl CF₃ C(CH₂CH₂) — — 3,3- dichloro- cyclo-butyl A1.612 Me Cl CF₃ CH₂— — 1-methyl- 2,2- dichloro- cyclo- propyl A1.613 Me Cl CF₃ CH₂ — —1-methyl- 2,2- dibromo- cyclo- propyl A1.614 Me Cl CF₃ CH₂ — — 2,2,3,3-tetrafluoro- cyclobutyl

FORMULATION EXAMPLES %=Percent by Weight

EXAMPLE F1 Emulsion concentrates a) b) c) Active ingredient 25% 40% 50%Calcium dodecylbenzenesulfonate 5% 8% 6% Castor oil polyethylene glycolether (36 mol of EO) 5% — — Tributylphenoxypolyethylene glycol — 12% 4%ether (30 mol of EO) Cyclohexanone — 15% 20% Xylene mixture 65% 25% 20%

Emulsions of any desired concentration can be prepared from suchconcentrates by dilution with water.

EXAMPLE F2 Solutions a) b) c) d) Active ingredient 80% 10% 5% 95%Ethylene glycol monomethyl ether 20% — — — Polyethylene glycol MW 400 —70% — — N-Methylpyrrolid-2-one — 20% — — Epoxidized coconut oil — — 1% 5% Petroleum ether (boiling range: 160-190°) — — 94%  —

The solutions are suitable for use in the form of microdrops.

EXAMPLE F3 Granules a) b) c) d) Active ingredient  5% 10%  8% 21% Kaolin94% — 79% 54% Highly disperse silica  1% — 13%  7% Attapulgite — 90% —18%

The active ingredient is dissolved in dichloromethane, the solution issprayed onto the carrier(s), and the solvent is subsequently evaporatedin vacuo.

EXAMPLE F4 Dusts a) b) Active ingredient 2% 5% Highly disperse silica 1%5% Talc 97%  — Kaolin — 90% 

Ready-to-use dusts are obtained by intimately mixing the carriers andthe active ingredient.

EXAMPLE F5 Wettable powders a) b) c) Active ingredient 25%  50% 75%Sodium lignosulfonate 5%  5% — Sodium lauryl sulfate 3% —  5% Sodium — 6% 10% diisobutylnaphthalenesulfonate Octylphenoxypolyethylene glycol — 2% — ether (7-8 mol of EO) Highly disperse silica 5% 10% 10% Kaolin62%  27% —

The active ingredient is mixed with the additives and the mixture isground thoroughly in a suitable mill. This gives wettable powders, whichcan be diluted with water to give suspensions of any desiredconcentration.

EXAMPLE F6 Extruder granules Active ingredient 10% Sodium lignosulfonate2% Carboxymethylcellulose 1% Kaolin 87%

The active ingredient is mixed with the additives, and the mixture isground, moistened with water, extruded, granulated and dried in a streamof air.

EXAMPLE F7 Coated granules Active ingredient 3% Polyethylene glycol (MW200) 3% Kaolin 94%

In a mixer, the finely ground active ingredient is applied uniformly tothe kaolin, which has been moistened with the polyethylene glycol. Thisgives dust-free coated granules.

EXAMPLE F8 Suspension concentrate Active ingredient 40% Ethylene glycol10% Nonylphenoxypolyethylene glycol ether (15 mol of EO)  6% Sodiumlignosulfonate 10% Carboxymethylcellulose  1% 37% aqueous formaldehydesolution 0.2%  Silicone oil (75% aqueous emulsion) 0.8%  Water 32%

The finely ground active ingredient is mixed intimately with theadditives. Suspensions of any desired concentration can be prepared fromthe thus resulting suspension concentrate by dilution with water.

The activity of the compositions according to the invention can bebroadened considerably, and adapted to prevailing circumstances, byadding other insecticidally, acaricidally and/or fungicidally activeingredients. Suitable additions to active ingredients here are, forexample, representatives of the following classes of active ingredients:organophosphorus compounds, nitrophenol derivatives, thioureas, juvenilehormones, formamidines, benzophenone derivatives, ureas, pyrrolederivatives, carbamates, pyrethroids, chlorinated hydrocarbons,acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoidsand Bacillus thuringiensis preparations.

The following mixtures of the compounds of formula I with activeingredients are preferred (the abbreviation “TX” means “one compoundselected from the group consisting of the compounds specificallydescribed in tables P, P′ and A of the present invention”):

-   -   an adjuvant selected from the group of substances consisting of        petroleum oils (alternative name) (628)+TX,    -   an acaricide selected from the group of substances consisting of        1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX,        2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts        name) (1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC        name) (1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name)        (981)+TX, abamectin (1)+TX, acequinocyl (3)+TX, acetoprole        [CCN]+TX, acrinathrin (9)+TX, aldicarb (16)+TX, aldoxycarb        (863)+TX, alpha-cypermethrin (202)+TX, amidithion (870)+TX,        amidoflumet [CCN]+TX, amidothioate (872)+TX, amiton (875)+TX,        amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, aramite        (881)+TX, arsenous oxide (882)+TX, AVI 382 (compound code)+TX,        AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX,        azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX,        azocyclotin (46)+TX, azothoate (889)+TX, benomyl (62)+TX,        benoxafos (alternative name) [CCN]+TX, benzoximate (71)+TX,        benzyl benzoate (IUPAC name) [CCN]+TX, bifenazate (74)+TX,        bifenthrin (76)+TX, binapacryl (907)+TX, brofenvalerate        (alternative name)+TX, bromocyclen (918)+TX, bromophos (920)+TX,        bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin        (99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX,        butylpyridaben (alternative name)+TX, calcium polysulfide (IUPAC        name) (111)+TX, camphechlor (941)+TX, carbanolate (943)+TX,        carbaryl (115)+TX, carbofuran (118)+TX, carbophenothion        (947)+TX, CGA 50'439 (development code) (125)+TX, chinomethionat        (126)+TX, chlorbenside (959)+TX, chlordimeform (964)+TX,        chlordimeform hydrochloride (964)+TX, chlorfenapyr (130)+TX,        chlorfenethol (968)+TX, chlorfenson (970)+TX, chlorfensulphide        (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate (975)+TX,        chloromebuform (977)+TX, chloromethiuron (978)+TX,        chloropropylate (983)+TX, chlorpyrifos (145)+TX,        chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX, cinerin I        (696)+TX, cinerin II (696)+TX, cinerins (696)+TX, clofentezine        (158)+TX, closantel (alternative name) [CCN]+TX, coumaphos        (174)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos        (1010)+TX, cufraneb (1013)+TX, cyanthoate (1020)+TX,        cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin        (196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM        (1032)+TX, DDT (219)+TX, demephion (1037)+TX, demephion-O        (1037)+TX, demephion-S (1037)+TX, demeton (1038)+TX,        demeton-methyl (224)+TX, demeton-O (1038)+TX, demeton-O-methyl        (224)+TX, demeton-S (1038)+TX, demeton-S-methyl (224)+TX,        demeton-S-methylsulphon (1039)+TX, diafenthiuron (226)+TX,        dialifos (1042)+TX, diazinon (227)+TX, dichlofluanid (230)+TX,        dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicofol        (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX, dimefox        (1081)+TX, dimethoate (262)+TX, dinactin (alternative name)        (653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton        (269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6        [CCN]+TX, dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon        (1097)+TX, dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl        sulfone (IUPAC name) (1103)+TX, disulfuram (alternative name)        [CCN]+TX, disulfoton (278)+TX, DNOC (282)+TX, dofenapyn        (1113)+TX, doramectin (alternative name) [CCN]+TX, endosulfan        (294)+TX, endothion (1121)+TX, EPN (297)+TX, eprinomectin        (alternative name) [CCN]+TX, ethion (309)+TX, ethoate-methyl        (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX, fenazaflor        (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX,        fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad        (alternative name)+TX, fenpyroximate (345)+TX, fenson (1157)+TX,        fentrifanil (1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX,        fluacrypyrim (360)+TX, fluazuron (1166)+TX, flubenzimine        (1167)+TX, flucycloxuron (366)+TX, flucythrinate (367)+TX,        fluenetil (1169)+TX, flufenoxuron (370)+TX, flumethrin (372)+TX,        fluorbenside (1174)+TX, fluvalinate (1184)+TX, FMC 1137        (development code) (1185)+TX, formetanate (405)+TX, formetanate        hydrochloride (405)+TX, formothion (1192)+TX, formparanate        (1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox        (424)+TX, heptenophos (432)+TX, hexadecyl        cyclopropanecarboxylate (IUPAC/Chemical Abstracts name)        (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPAC name)        (542)+TX, isocarbophos (alternative name) (473)+TX, isopropyl        O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,        ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX,        jasmolin II (696)+TX, jodfenphos (1248)+TX, lindane (430)+TX,        lufenuron (490)+TX, malathion (492)+TX, malonoben (1254)+TX,        mecarbam (502)+TX, mephosfolan (1261)+TX, mesulfen (alternative        name) [CCN]+TX, methacrifos (1266)+TX, methamidophos (527)+TX,        methidathion (529)+TX, methiocarb (530)+TX, methomyl (531)+TX,        methyl bromide (537)+TX, metolcarb (550)+TX, mevinphos (556)+TX,        mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime        (alternative name) [CCN]+TX, mipafox (1293)+TX, monocrotophos        (561)+TX, morphothion (1300)+TX, moxidectin (alternative name)        [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512        (compound code)+TX, nifluridide (1309)+TX, nikkomycins        (alternative name) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb        1:1 zinc chloride complex (1313)+TX, NNI-0101 (compound        code)+TX, NNI-0250 (compound code)+TX, omethoate (594)+TX,        oxamyl (602)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX,        pp′-DDT (219)+TX, parathion (615)+TX, permethrin (626)+TX,        petroleum oils (alternative name) (628)+TX, phenkapton        (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone        (637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon        (639)+TX, phoxim (642)+TX, pirimiphos-methyl (652)+TX,        polychloroterpenes (traditional name) (1347)+TX, polynactins        (alternative name) (653)+TX, proclonol (1350)+TX, profenofos        (662)+TX, promacyl (1354)+TX, propargite (671)+TX, propetamphos        (673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothoate        (1362)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX,        pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion        (701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos        (711)+TX, quintiofos (1381)+TX, R-1492 (development code)        (1382)+TX, RA-17 (development code) (1383)+TX, rotenone        (722)+TX, schradan (1389)+TX, sebufos (alternative name)+TX,        selamectin (alternative name) [CCN]+TX, SI-0009 (compound        code)+TX, sophamide (1402)+TX, spirodiclofen (738)+TX,        spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX,        sulfuram (alternative name) [CCN]+TX, sulfluramid (750)+TX,        sulfotep (753)+TX, sulfur (754)+TX, SZI-121 (development code)        (757)+TX, tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP        (1417)+TX, terbam (alternative name)+TX, tetrachlorvinphos        (777)+TX, tetradifon (786)+TX, tetranactin (alternative name)        (653)+TX, tetrasul (1425)+TX, thiafenox (alternative name)+TX,        thiocarboxime (1431)+TX, thiofanox (800)+TX, thiometon (801)+TX,        thioquinox (1436)+TX, thuringiensin (alternative name) [CCN]+TX,        triamiphos (1441)+TX, triarathene (1443)+TX, triazophos        (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX,        trifenofos (1455)+TX, trinactin (alternative name) (653)+TX,        vamidothion (847)+TX, vaniliprole [CCN] and yl-5302 (compound        code)+TX,    -   an algicide selected from the group of substances consisting of        bethoxazin [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX,        copper sulfate (172)+TX, cybutryne [CCN]+TX, dichlone (1052)+TX,        dichlorophen (232)+TX, endothal (295)+TX, fentin (347)+TX,        hydrated lime [CCN]+TX, nabam (566)+TX, quinoclamine (714)+TX,        quinonamid (1379)+TX, simazine (730)+TX, triphenyltin acetate        (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name)        (347)+TX,    -   an anthelmintic selected from the group of substances consisting        of abamectin (1)+TX, crufomate (1011)+TX, doramectin        (alternative name) [CCN]+TX, emamectin (291)+TX, emamectin        benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX,        ivermectin (alternative name) [CCN]+TX, milbemycin oxime        (alternative name) [CCN]+TX, moxidectin (alternative name)        [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name)        [CCN]+TX, spinosad (737) and thiophanate (1435)+TX,    -   an avicide selected from the group of substances consisting of        chloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX,        pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX,    -   a bactericide selected from the group of substances consisting        of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX,        4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name)        (748)+TX, 8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX,        copper dioctanoate (IUPAC name) (170)+TX, copper hydroxide        (IUPAC name) (169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX,        dipyrithione (1105)+TX, dodicin (1112)+TX, fenaminosulf        (1144)+TX, formaldehyde (404)+TX, hydrargaphen (alternative        name) [CCN]+TX, kasugamycin (483)+TX, kasugamycin hydrochloride        hydrate (483)+TX, nickel bis(dimethyldithiocarbamate) (IUPAC        name) (1308)+TX, nitrapyrin (580)+TX, octhilinone (590)+TX,        oxolinic acid (606)+TX, oxytetracycline (611)+TX, potassium        hydroxyquinoline sulfate (446)+TX, probenazole (658)+TX,        streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX,        tecloftalam (766)+TX, and thiomersal (alternative name)        [CCN]+TX,    -   a biological agent selected from the group of substances        consisting of Adoxophyes orana GV (alternative name) (12)+TX,        Agrobacterium radiobacter (alternative name) (13)+TX, Amblyseius        spp. (alternative name) (19)+TX, Anagrapha falcifera NPV        (alternative name) (28)+TX, Anagrus atomus (alternative name)        (29)+TX, Aphelinus abdominalis (alternative name) (33)+TX,        Aphidius colemani (alternative name) (34)+TX, Aphidoletes        aphidimyza (alternative name) (35)+TX, Autographa californica        NPV (alternative name) (38)+TX, Bacillus firmus (alternative        name) (48)+TX, Bacillus sphaericus Neide (scientific name)        (49)+TX, Bacillus thuringiensis Berliner (scientific name)        (51)+TX, Bacillus thuringiensis subsp. aizawai (scientific name)        (51)+TX, Bacillus thuringiensis subsp. israelensis (scientific        name) (51)+TX, Bacillus thuringiensis subsp. japonensis        (scientific name) (51)+TX, Bacillus thuringiensis subsp.        kurstaki (scientific name) (51)+TX, Bacillus thuringiensis        subsp. tenebrionis (scientific name) (51)+TX, Beauveria bassiana        (alternative name) (53)+TX, Beauveria brongniartfii (alternative        name) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX,        Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia        pomonella GV (alternative name) (191)+TX, Dacnusa sibirica        (alternative name) (212)+TX, Diglyphus isaea (alternative name)        (254)+TX, Encarsia formosa (scientific name) (293)+TX,        Eretmocerus eremicus (alternative name) (300)+TX, Helicoverpa        zea NPV (alternative name) (431)+TX, Heterorhabditis        bacteriophora and H. megidis (alternative name) (433)+TX,        Hippodamia convergens (alternative name) (442)+TX, Leptomastix        dactylopii (alternative name) (488)+TX, Macrolophus caliginosus        (alternative name) (491)+TX, Mamestra brassicae NPV (alternative        name) (494)+TX, Metaphycus helvolus (alternative name) (522)+TX,        Metarhizium anisopliae var. acridum (scientific name) (523)+TX,        Metarhizium anisopliae var. anisopliae (scientific name)        (523)+TX, Neodiprion sertifer NPV and N. lecontei NPV        (alternative name) (575)+TX, Orius spp. (alternative name)        (596)+TX, Paecilomyces fumosoroseus (alternative name) (613)+TX,        Phytoseiulus persimilis (alternative name) (644)+TX, Spodoptera        exigua multicapsid nuclear polyhedrosis virus (scientific name)        (741)+TX, Steinemema bibionis (alternative name) (742)+TX,        Steinernema carpocapsae (alternative name) (742)+TX, Steinernema        feltiae (alternative name) (742)+TX, Steinernema glaseri        (alternative name) (742)+TX, Steinernema riobrave (alternative        name) (742)+TX, Steinernema riobravis (alternative name)        (742)+TX, Steinernema scapterisci (alternative name) (742)+TX,        Steinernema spp. (alternative name) (742)+TX, Trichogramma spp.        (alternative name) (826)+TX, Typhlodromus occidentalis        (alternative name) (844) and Verticillium lecanii (alternative        name) (848)+TX,    -   a soil sterilant selected from the group of substances        consisting of iodomethane (IUPAC name) (542) and methyl bromide        (537)+TX,    -   a chemosterilant selected from the group of substances        consisting of apholate [CCN]+TX, bisazir (alternative name)        [CCN]+TX, busulfan (alternative name) [CCN]+TX, diflubenzuron        (250)+TX, dimatif (alternative name) (CCN)+TX, hemel (CCN)+TX,        hempa [CCN]+TX, metepa [CCN]+TX, methiotepa [CCN]+TX, methyl        apholate [CCN]+TX, morzid [CCN]+TX, penfluoron (alternative        name) [CCN]+TX, tepa [CCN]+TX, thiohempa (alternative name)        [CCN]+TX, thiotepa (alternative name) [CCN]+TX, tretamine        (alternative name) [CCN] and uredepa (alternative name)        [CCN]+TX,    -   an insect pheromone selected from the group of substances        consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol        (IUPAC name) (222)+TX, (E)-tridec-4-en-1-yl acetate (IUPAC name)        (829)+TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX,        (E+TX, Z)-tetradeca-4+TX, 10-dien-1-yl acetate (IUPAC name)        (779)+TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX,        (Z)-hexadec-11-enal (IUPAC name) (436)+TX,        (Z)-hexadec-11-en-1-yl acetate (IUPAC name) (437)+TX,        (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX,        (Z)-icos-13-en-10-one (IUPAC name) (448)+TX,        (Z)-tetradec-7-en-1-al (IUPAC name) (782)+TX,        (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX,        (Z)-tetradec-9-en-11-yl acetate (IUPAC name) (784)+TX, (7E+TX,        9z)-dodeca-7+TX, 9-dien-1-yl acetate (IUPAC name) (283)+TX,        (9Z+TX, 11E)-tetradeca-9+TX, 11-dien-1-yl acetate (IUPAC name)        (780)+TX, (9Z+TX, 12E)-tetradeca-9+TX, 12-dien-1-yl acetate        (IUPAC name) (781)+TX, 14-methyloctadec-1-ene (IUPAC name)        (545)+TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC        name) (544)+TX, alpha-multistriatin (alternative name) [CCN]+TX,        brevicomin (alternative name) (CCN)+TX, codlelure (alternative        name) [CCN]+TX, codlemone (alternative name) (167)+TX, cuelure        (alternative name) (179)+TX, disparlure (277)+TX,        dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl        acetate (IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate        (IUPAC name) (284)+TX, dominicalure (alternative name) [CCN]+TX,        ethyl 4-methyloctanoate (IUPAC name) (317)+TX, eugenol        (alternative name) [CCN]+TX, frontalin (alternative name)        [CCN]+TX, gossyplure (alternative name) (420)+TX, grandlure        (421)+TX, grandlure I (alternative name) (421)+TX, grandlure II        (alternative name) (421)+TX, grandlure III (alternative name)        (421)+TX, grandlure IV (alternative name) (421)+TX, hexylure        [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol        (alternative name) [CCN]+TX, japonilure (alternative name)        (481)+TX, lineatin (alternative name) [CCN]+TX, litiure        (alternative name) [CCN]+TX, looplure (alternative name)        [CCN]+TX, medlure [CCN]+TX, megatomoic acid (alternative name)        [CCN]+TX, methyl eugenol (alternative name) (540)+TX, muscalure        (563)+TX, octadeca-2+TX, 13-dien-1-yl acetate (IUPAC name)        (588)+TX, octadeca-3+TX, 13-dien-1-yl acetate (IUPAC name)        (589)+TX, orfralure (alternative name) [CCN]+TX, oryctalure        (alternative name) (317)+TX, ostramone (alternative name)        [CCN]+TX, sigiure [CCN]+TX, sordidin (alternative name)        (736)+TX, sulcatol (alternative name) [CCN]+TX,        tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, trimedlure        (839)+TX, trimedlure A (alternative name) (839)+TX, trimedlure        B, (alternative name) (839)+TX, trimedlure B₂ (alternative name)        (839)+TX, trimedlure C (alternative name) (839) and trunc-call        (alternative name) [CCN]+TX,    -   an insect repellent selected from the group of substances        consisting of 2-(octylthio)-ethanol (IUPAC name) (591)+TX,        butopyronoxyl (933)+TX, butoxy(polypropylene glycol) (936)+TX,        dibutyl adipate (IUPAC name) (1046)+TX, dibutyl phthalate        (1047)+TX, dibutyl succinate (IUPAC name) (1048)+TX,        diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX, dimethyl        phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide        [CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide        [CCN]+TX, oxamate [CCN] and picaridin [CCN]+TX,    -   an insecticide selected from the group of substances consisting        of 1+TX, 1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts        name) (1058)+TX, 1+TX, 1-dichloro-2+TX,        2-bis(4-ethylphenyl)ethane (IUPAC name) (1056)+TX, 1+TX,        2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX,        1+TX, 2-dichloropropane with 1+TX, 3-dichloropropene (IUPAC        name) (1063)+TX, 1-bromo-2-chloroethane (IUPAC/Chemical        Abstracts name) (916)+TX, 2+TX, 2+TX, 2-trichloro-1-(3+TX,        4-dichlorophenyl)ethyl acetate (IUPAC name) (1451)+TX, 2+TX,        2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate (IUPAC        name) (1066)+TX, 2-(1+TX, 3-dithiolan-2-yl)phenyl        dimethylcarbamate (IUPAC/Chemical Abstracts name) (1109)+TX,        2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts        name) (935)+TX, 2-(4+TX, 5-dimethyl-1+TX, 3-dioxolan-2-yl)phenyl        methylcarbamate (IUPAC/Chemical Abstracts name) (1084)+TX,        2-(4-chloro-3+TX, 5-xylyloxy)ethanol (IUPAC name) (986)+TX,        2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX,        2-imidazolidone (IUPAC name) (1225)+TX, 2-isovalerylindan-1+TX,        3-dione (IUPAC name) (1246)+TX, 2-methyl(prop-2-ynyl)aminophenyl        methylcarbamate (IUPAC name) (1284)+TX, 2-thiocyanatoethyl        laurate (IUPAC name) (1433)+TX, 3-bromo-1-chloroprop-1-ene        (IUPAC name) (917)+TX, 3-methyl-1-phenylpyrazol-5-yl        dimethylcarbamate (IUPAC name) (1283)+TX,        4-methyl(prop-2-ynyl)amino-3+TX, 5-xylyl methylcarbamate (IUPAC        name) (1285)+TX, 5+TX, 5-dimethyl-3-oxocyclohex-1-enyl        dimethylcarbamate (IUPAC name) (1085)+TX, abamectin (1)+TX,        acephate (2)+TX, acetamiprid (4)+TX, acethion (alternative name)        [CCN]+TX, acetoprole [CCN]+TX, acrinathrin (9)+TX, acrylonitrile        (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb (16)+TX,        aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX,        allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX,        alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name)        [CCN]+TX, aluminium phosphide (640)+TX, amidithion (870)+TX,        amidothioate (872)+TX, aminocarb (873)+TX, amiton (875)+TX,        amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, anabasine        (877)+TX, athidathion (883)+TX, AVI 382 (compound code)+TX, AZ        60541 (compound code)+TX, azadirachtin (alternative name)        (41)+TX, azamethiphos (42)+TX, azinphos-ethyl (44)+TX,        azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillus        thuringiensis delta endotoxins (alternative name) (52)+TX,        barium hexafluorosilicate (alternative name) [CCN]+TX, barium        polysulfide (IUPAC/Chemical Abstracts name) (892)+TX, barthrin        [CCN]+TX, Bayer 22/190 (development code) (893)+TX, Bayer 22408        (development code) (894)+TX, bendiocarb (58)+TX, benfuracarb        (60)+TX, bensultap (66)+TX, beta-cyfluthrin (194)+TX,        beta-cypermethrin (203)+TX, bifenthrin (76)+TX, bioallethrin        (78)+TX, bioallethrin S-cyclopentenyl isomer (alternative name)        (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin (908)+TX,        bioresmethrin (80)+TX, bis(2-chloroethyl)ether (IUPAC name)        (909)+TX, bistrifluoron (83)+TX, borax (86)+TX, brofenvalerate        (alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen        (918)+TX, bromo-DDT (alternative name) [CCN]+TX, bromophos        (920)+TX, bromophos-ethyl (921)+TX, bufencarb (924)+TX,        buprofezin (99)+TX, butacarb (926)+TX, butathiofos (927)+TX,        butocarboxim (103)+TX, butonate (932)+TX, butoxycarboxim        (104)+TX, butylpyridaben (alternative name)+TX, cadusafos        (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX,        calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX,        carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX,        carbon disulfide (IUPAC/Chemical Abstracts name) (945)+TX,        carbon tetrachloride (IUPAC name) (946)+TX, carbophenothion        (947)+TX, carbosulfan (119)+TX, cartap (123)+TX, cartap        hydrochloride (123)+TX, cevadine (alternative name) (725)+TX,        chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone        (963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride        (964)+TX, chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX,        chlorfenvinphos (131)+TX, chlorfluazuron (132)+TX, chlormephos        (136)+TX, chloroform [CCN]+TX, chloropicrin (141)+TX,        chlorphoxim (989)+TX, chlorprazophos (990)+TX, chlorpyrifos        (145)+TX, chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX,        chromafenozide (150)+TX, cinerin I (696)+TX, cinerin II        (696)+TX, cinerins (696)+TX, cis-resmethrin (alternative        name)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX,        cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX,        clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper        arsenate [CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX,        coumithoate (1006)+TX, crotamiton (alternative name) [CCN]+TX,        crotoxyphos (1010)+TX, crufomate (1011)+TX, cryolite        (alternative name) (177)+TX, CS 708 (development code)        (1012)+TX, cyanofenphos (1019)+TX, cyanophos (184)+TX,        cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin        (188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX,        cypermethrin (201)+TX, cyphenothrin (206)+TX, cyromazine        (209)+TX, cythioate (alternative name) [CCN]+TX, d-limonene        (alternative name) [CCN]+TX, d-tetramethrin (alternative name)        (788)+TX, DAEP (1031)+TX, dazomet (216)+TX, DDT (219)+TX,        decarbofuran (1034)+TX, deltamethrin (223)+TX, demephion        (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX, demeton        (1038)+TX, demetonmethyl (224)+TX, demeton-O (1038)+TX,        demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl        (224)+TX, demeton-S-methylsulphon (1039)+TX, diafenthiuron        (226)+TX, dialifos (1042)+TX, diamidafos (1044)+TX, diazinon        (227)+TX, dicapthon (1050)+TX, dichlofenthion (1051)+TX,        dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicresyl        (alternative name) [CCN]+TX, dicrotophos (243)+TX, dicyclanil        (244)+TX, dieldrin (1070)+TX, diethyl 5-methylpyrazol-3-yl        phosphate (IUPAC name) (1076)+TX, diflubenzuron (250)+TX, dilor        (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX, dimefox        (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin        (1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex        (1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX,        dinosam (1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX,        diofenolan (1099)+TX, dioxabenzofos (1100)+TX, dioxacarb        (1101)+TX, dioxathion (1102)+TX, disulfoton (278)+TX,        dithicrofos (1108)+TX, DNOC (282)+TX, doramectin (alternative        name) [CCN]+TX, DSP (1115)+TX, ecdysterone (alternative name)        [CCN]+TX, EI 1642 (development code) (1118)+TX, emamectin        (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX,        empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX,        endrin (1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane        (1124)+TX, eprinomectin (alternative name) [CCN]+TX,        esfenvalerate (302)+TX, etaphos (alternative name) [CCN]+TX,        ethiofencarb (308)+TX, ethion (309)+TX, ethiprole (310)+TX,        ethoate-methyl (1134)+TX, ethoprophos (312)+TX, ethyl formate        (IUPAC name) [CCN]+TX, ethyl-DDD (alternative name) (1056)+TX,        ethylene dibromide (316)+TX, ethylene dichloride (chemical name)        (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX,        etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos        (326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX,        fenethacarb (1149)+TX, fenfluthrin (1150)+TX, fenitrothion        (335)+TX, fenobucarb (336)+TX, fenoxacrim (1153)+TX, fenoxycarb        (340)+TX, fenpirithrin (1155)+TX, fenpropathrin (342)+TX,        fenpyrad (alternative name)+TX, fensulfothion (1158)+TX,        fenthion (346)+TX, fenthion-ethyl [CCN]+TX, fenvalerate        (349)+TX, fipronil (354)+TX, flonicamid (358)+TX, flubendiamide        (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX,        flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil        (1169)+TX, flufenerim [CCN]+TX, flufenoxuron (370)+TX,        flufenprox (1171)+TX, flumethrin (372)+TX, fluvalinate        (1184)+TX, FMC 1137 (development code) (1185)+TX, fonofos        (1191)+TX, formetanate (405)+TX, formetanate hydrochloride        (405)+TX, formothion (1192)+TX, formparanate (1193)+TX,        fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate        (408)+TX, fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin        (1200)+TX, gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX,        guazatine (422)+TX, guazatine acetates (422)+TX, GY-81        (development code) (423)+TX, halfenprox (424)+TX, halofenozide        (425)+TX, HCH (430)+TX, HEOD (1070)+TX, heptachlor (1211)+TX,        heptenophos (432)+TX, heterophos [CCN]+TX, hexaflumuron        (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX, hydrogen        cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX,        imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb        (465)+TX, iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX,        isazofos (1231)+TX, isobenzan (1232)+TX, isocarbophos        (alternative name) (473)+TX, isodrin (1235)+TX, isofenphos        (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX, isopropyl        O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,        isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion        (480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I        (696)+TX, jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile        hormone I (alternative name) [CCN]+TX, juvenile hormone II        (alternative name) [CCN]+TX, juvenile hormone III (alternative        name) [CCN]+TX, kelevan (1249)+TX, kinoprene (484)+TX,        lambda-cyhalothrin (198)+TX, lead arsenate [CCN]+TX, lepimectin        (CCN)+TX, leptophos (1250)+TX, lindane (430)+TX, lirimfos        (1251)+TX, lufenuron (490)+TX, lythidathion (1253)+TX, m-cumenyl        methylcarbamate (IUPAC name) (1014)+TX, magnesium phosphide        (IUPAC name) (640)+TX, malathion (492)+TX, malonoben (1254)+TX,        mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX,        menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride        (513)+TX, mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam        (519)+TX, metam-potassium (alternative name) (519)+TX,        metam-sodium (519)+TX, methacrifos (1266)+TX, methamidophos        (527)+TX, methanesulfonyl fluoride (IUPAC/Chemical Abstracts        name) (1268)+TX, methidathion (529)+TX, methiocarb (530)+TX,        methocrotophos (1273)+TX, methomyl (531)+TX, methoprene        (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternative        name) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX,        methyl bromide (537)+TX, methyl isothiocyanate (543)+TX,        methylchloroform (alternative name) [CCN]+TX, methylene chloride        [CCN]+TX, metofluthrin [CCN]+TX, metolcarb (550)+TX,        metoxadiazone (1288)+TX, mevinphos (556)+TX, mexacarbate        (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative        name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX,        monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin        (alternative name) [CCN]+TX, naftalofos (alternative name)        [CCN]+TX, naled (567)+TX, naphthalene (IUPAC/Chemical Abstracts        name) (1303)+TX, NC-170 (development code) (1306)+TX, NC-184        (compound code)+TX, nicotine (578)+TX, nicotine sulfate        (578)+TX, nifluridide (1309)+TX, nitenpyram (579)+TX, nithiazine        (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloride        complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250        (compound code)+TX, nornicotine (traditional name) (1319)+TX,        novaluron (585)+TX, noviflumuron (586)+TX,        O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (IUPAC        name) (1057)+TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl        phosphorothioate (IUPAC name) (1074)+TX, O,O-diethyl        O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name)        (1075)+TX, O,O,O′,O′-tetrapropyl dithiopyrophosphate (IUPAC        name) (1424)+TX, oleic acid (IUPAC name) (593)+TX, omethoate        (594)+TX, oxamyl (602)+TX, oxydemeton-methyl (609)+TX,        oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT        (219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX,        parathion-methyl (616)+TX, penfluoron (alternative name)        [CCN]+TX, pentachlorophenol (623)+TX, pentachlorophenyl laurate        (IUPAC name) (623)+TX, permethrin (626)+TX, petroleum oils        (alternative name) (628)+TX, PH 60-38 (development code)        (1328)+TX, phenkapton (1330)+TX, phenothrin (630)+TX, phenthoate        (631)+TX, phorate (636)+TX, phosalone (637)+TX, phosfolan        (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX, phosphamidon        (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX,        phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb        (651)+TX, pirimiphos-ethyl (1345)+TX, pirimiphos-methyl        (652)+TX, polychlorodicyclopentadiene isomers (IUPAC name)        (1346)+TX, polychloroterpenes (traditional name) (1347)+TX,        potassium arsenite [CCN]+TX, potassium thiocyanate [CCN]+TX,        prallethrin (655)+TX, precocene I (alternative name) [CCN]+TX,        precocene II (alternative name) [CCN]+TX, precocene II        (alternative name) [CCN]+TX, primidophos (1349)+TX, profenofos        (662)+TX, profluthrin [CCN]+TX, promacyl (1354)+TX, promecarb        (1355)+TX, propaphos (1356)+TX, propetamphos (673)+TX, propoxur        (678)+TX, prothidathion (1360)+TX, prothiofos (686)+TX,        prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine        (688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin        (1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX,        pyrethrins (696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX,        pyridaphenthion (701)+TX, pyrimidifen (706)+TX, pyrimitate        (1370)+TX, pyriproxyfen (708)+TX, quassia (alternative name)        [CCN]+TX, quinalphos (711)+TX, quinalphosmethyl (1376)+TX,        quinothion (1380)+TX, quintiofos (1381)+TX, R-1492 (development        code) (1382)+TX, rafoxanide (alternative name) [CCN]+TX,        resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (development        code) (723)+TX, RU 25475 (development code) (1386)+TX, ryania        (alternative name) (1387)+TX, ryanodine (traditional name)        (1387)+TX, sabadilla (alternative name) (725)+TX, schradan        (1389)+TX, sebufos (alternative name)+TX, selamectin        (alternative name) [CCN]+TX, SI-0009 (compound code)+TX, SI-0205        (compound code)+TX, SI-0404 (compound code)+TX, SI-0405        (compound code)+TX, silafluofen (728)+TX, SN 72129 (development        code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide        (444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name)        (1399)+TX, sodium hexafluorosilicate (1400)+TX, sodium        pentachlorophenoxide (623)+TX, sodium selenate (IUPAC name)        (1401)+TX, sodium thiocyanate [CCN]+TX, sophamide (1402)+TX,        spinosad (737)+TX, spiromesifen (739)+TX, spirotetrmat (CCN)+TX,        sulcofuron (746)+TX, sulcofuronsodium (746)+TX, sulfluramid        (750)+TX, sulfotep (753)+TX, sulfuryl fluoride (756)+TX,        sulprofos (1408)+TX, tar oils (alternative name) (758)+TX,        tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX,        tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos        (764)+TX, teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos        (770)+TX, TEPP (1417)+TX, terallethrin (1418)+TX, terbam        (alternative name)+TX, terbufos (773)+TX, tetrachloroethane        [CCN]+TX, tetrachlorvinphos (777)+TX, tetramethrin (787)+TX,        theta-cypermethrin (204)+TX, thiacloprid (791)+TX, thiafenox        (alternative name)+TX, thiamethoxam (792)+TX, thicrofos        (1428)+TX, thiocarboxime (1431)+TX, thiocyclam (798)+TX,        thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX,        thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX,        thiosultap (803)+TX, thiosultap-sodium (803)+TX, thuringiensin        (alternative name) [CCN]+TX, tolfenpyrad (809)+TX, tralomethrin        (812)+TX, transfluthrin (813)+TX, transpermethrin (1440)+TX,        triamiphos (1441)+TX, triazamate (818)+TX, triazophos (820)+TX,        triazuron (alternative name)+TX, trichlorfon (824)+TX,        trichlormetaphos-3 (alternative name) [CCN]+TX, trichloronat        (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX,        trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX,        vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX,        veratrine (alternative name) (725)+TX, XMC (853)+TX, xylylcarb        (854)+TX, yl-5302 (compound code)+TX, zeta-cypermethrin        (205)+TX, zetamethrin (alternative name)+TX, zinc phosphide        (640)+TX, zolaprofos (1469) and ZXI 8901 (development code)        (858)+TX,    -   a molluscicide selected from the group of substances consisting        of bis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide        [CCN]+TX, calcium arsenate [CCN]+TX, cloethocarb (999)+TX,        copper acetoarsenite [CCN]+TX, copper sulfate (172)+TX, fentin        (347)+TX, ferric phosphate (IUPAC name) (352)+TX, metaldehyde        (518)+TX, methiocarb (530)+TX, niclosamide (576)+TX,        niclosamide-olamine (576)+TX, pentachlorophenol (623)+TX, sodium        pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX, thiodicarb        (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX,        trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347)        and triphenyltin hydroxide (IUPAC name) (347)+TX,    -   a nematicide selected from the group of substances consisting of        AKD-3088 (compound code)+TX, 1+TX, 2-dibromo-3-chloropropane        (IUPAC/Chemical Abstracts name) (1045)+TX, 1+TX,        2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX,        1+TX, 2-dichloropropane with 1+TX, 3-dichloropropene (IUPAC        name) (1063)+TX, 1+TX, 3-dichloropropene (233)+TX, 3+TX,        4-dichlorotetrahydrothiophene 1+TX, 1-dioxide (IUPAC/Chemical        Abstracts name) (1065)+TX, 3-(4-chlorophenyl)-5-methylrhodanine        (IUPAC name) (980)+TX, 5-methyl-6-thioxo-1+TX, 3+TX,        5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286)+TX,        6-isopentenylaminopurine (alternative name) (210)+TX, abamectin        (1)+TX, acetoprole [CCN]+TX, alanycarb (15)+TX, aldicarb        (16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX,        benclothiaz [CCN]+TX, benomyl (62)+TX, butylpyridaben        (alternative name)+TX, cadusafos (109)+TX, carbofuran (118)+TX,        carbon disulfide (945)+TX, carbosulfan (119)+TX, chloropicrin        (141)+TX, chlorpyrifos (145)+TX, cloethocarb (999)+TX,        cytokinins (alternative name) (210)+TX, dazomet (216)+TX, DBCP        (1045)+TX, DCIP (218)+TX, diamidafos (1044)+TX, dichlofenthion        (1051)+TX, dicliphos (alternative name)+TX, dimethoate (262)+TX,        doramectin (alternative name) [CCN]+TX, emamectin (291)+TX,        emamectin benzoate (291)+TX, eprinomectin (alternative name)        [CCN]+TX, ethoprophos (312)+TX, ethylene dibromide (316)+TX,        fenamiphos (326)+TX, fenpyrad (alternative name)+TX,        fensulfothion (1158)+TX, fosthiazate (408)+TX, fosthietan        (1196)+TX, furfural (alternative name) [CCN]+TX, GY-81        (development code) (423)+TX, heterophos [CCN]+TX, iodomethane        (IUPAC name) (542)+TX, isamidofos (1230)+TX, isazofos (1231)+TX,        ivermectin (alternative name) [CCN]+TX, kinetin (alternative        name) (210)+TX, mecarphon (1258)+TX, metam (519)+TX,        metam-potassium (alternative name) (519)+TX, metam-sodium        (519)+TX, methyl bromide (537)+TX, methyl isothiocyanate        (543)+TX, milbemycin oxime (alternative name) [CCN]+TX,        moxidectin (alternative name) [CCN]+TX, Myrothecium verrucaria        composition (alternative name) (565)+TX, NC-184 (compound        code)+TX, oxamyl (602)+TX, phorate (636)+TX, phosphamidon        (639)+TX, phosphocarb [CCN]+TX, sebufos (alternative name)+TX,        selamectin (alternative name) [CCN]+TX, spinosad (737)+TX,        terbam (alternative name)+TX, terbufos (773)+TX,        tetrachlorothiophene (IUPAC/Chemical Abstracts name) (1422)+TX,        thiafenox (alternative name)+TX, thionazin (1434)+TX, triazophos        (820)+TX, triazuron (alternative name)+TX, xylenols [CCN]+TX,        yl-5302 (compound code) and zeatin (alternative name) (210)+TX,    -   a nitrification inhibitor selected from the group of substances        consisting of potassium ethylxanthate [CCN] and nitrapyrin        (580)+TX,    -   a plant activator selected from the group of substances        consisting of acibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX,        probenazole (658) and Reynoutria sachalinensis extract        (alternative name) (720)+TX,    -   a rodenticide selected from the group of substances consisting        of 2-isovalerylindan-1+TX, 3-dione (IUPAC name) (1246)+TX,        4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name)        (748)+TX, alpha-chlorohydrin [CCN]+TX, aluminium phosphide        (640)+TX, antu (880)+TX, arsenous oxide (882)+TX, barium        carbonate (891)+TX, bisthiosemi (912)+TX, brodifacoum (89)+TX,        bromadiolone (91)+TX, bromethalin (92)+TX, calcium cyanide        (444)+TX, chloralose (127)+TX, chlorophacinone (140)+TX,        cholecalciferol (alternative name) (850)+TX, coumachlor        (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX,        crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX,        diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen        (357)+TX, fluoroacetamide (379)+TX, flupropadine (1183)+TX,        flupropadine hydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH        (430)+TX, hydrogen cyanide (444)+TX, iodomethane (IUPAC name)        (542)+TX, lindane (430)+TX, magnesium phosphide (IUPAC name)        (640)+TX, methyl bromide (537)+TX, norbormide (1318)+TX,        phosacetim (1336)+TX, phosphine (IUPAC name) (640)+TX,        phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite        (CCN)+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium        arsenite [CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate        (735)+TX, strychnine (745)+TX, thallium sulfate [CCN]+TX,        warfarin (851) and zinc phosphide (640)+TX,    -   a synergist selected from the group of substances consisting of        2-(2-butoxyethoxy)-ethyl piperonylate (IUPAC name) (934)+TX,        5-(1+TX, 3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC        name) (903)+TX, farnesol with nerolidol (alternative name)        (324)+TX, MB-599 (development code) (498)+TX, MGK 264        (development code) (296)+TX, piperonyl butoxide (649)+TX,        piprotal (1343)+TX, propyl isomer (1358)+TX, S421 (development        code) (724)+TX, sesamex (1393)+TX, sesasmolin (1394) and        sulfoxide (1406)+TX,    -   an animal repellent selected from the group of substances        consisting of anthraquinone (32)+TX, chloralose (127)+TX, copper        naphthenate [CCN]+TX, copper oxychloride (171)+TX, diazinon        (227)+TX, dicyclopentadiene (chemical name) (1069)+TX, guazatine        (422)+TX, guazatine acetates (422)+TX, methiocarb (530)+TX,        pyridin-4-amine (IUPAC name) (23)+TX, thiram (804)+TX,        trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram        (856)+TX,    -   a virucide selected from the group of substances consisting of        imanin (alternative name) [CCN] and ribavirin (alternative name)        [CCN]+TX,    -   and a wound protectant selected from the group of substances        consisting of mercuric oxide (512)+TX, octhilinone (590) and        thiophanate-methyl (802)+TX, the compound of formula A-1

the formula A-2

the formula A-3

the formula A-4

the formula A-5

the formula A-6

the formula A-7

the formula A-8

the formula A-9

the formula A-10

the formula A-11

the formula A-12

the formula A-13

the formula A-14

the formula A-15

the formula A-16

the formula A-17

the formula A-18

the formula A-19

the formula A-20

the formula A-21

the formula A-22

the formula A-23

the formula A-24

the formula A-25

the formula A-26

and Azaconazole (60207-31-0]+TX, Bitertanol [70585-36-3]+TX,Bromuconazole [116255-48-2]+TX, Cyproconazole [94361-06-5]+TX,Difenoconazole [119446-68-3]+TX, Diniconazole [83657-24-3]+TX,Epoxiconazole [106325-08-0]+TX, Fenbuconazole [114369-43-6]+TX,Fluquinconazole [136426-54-5]+TX, Flusilazole [85509-19-9]+TX,Flutriafol [76674-21-0]+TX, Hexaconazole [79983-71-4]+TX, Imazalil[35554-44-0]+TX, Imibenconazole [86598-92-7]+TX, Ipconazole[125225-28-7]+TX, Metconazole [125116-23-6]+TX, Myclobutanil[88671-89-0]+TX, Pefurazoate [101903-30-4]+TX, Penconazole[66246-88-6]+TX, Prothioconazole [178928-70-6]+TX, Pyrifenox[88283-41-4]+TX, Prochloraz [67747-09-5]+TX, Propiconazole[60207-90-1]+TX, Simeconazole [149508-90-7]+TX, Tebuconazole[107534-96-3]+TX, Tetraconazole [112281-77-3]+TX, Triadimefon[43121-43-3]+TX, Triadimenol [55219-65-3]+TX, Triflumizole[99387-89-0]+TX, Triticonazole [131983-72-7]+TX, Ancymidol[12771-68-5]+TX, Fenarimol [60168-88-9]+TX, Nuarimol [63284-71-9]+TX,Bupirimate [41483-43-6]+TX, Dimethirimol [5221-53-4]+TX, Ethirimol[23947-60-6]+TX, Dodemorph [1593-77-7]+TX, Fenpropidine [67306-00-7]+TX,Fenpropimorph [67564-91-4]+TX, Spiroxamine [118134-30-8]+TX, Tridemorph[81412-43-3]+TX, Cyprodinil [121552-61-2]+TX, Mepanipyrim[110235-47-7]+TX, Pyrimethanil [53112-28-0]+TX, Fenpiclonil[74738-17-3]+TX, Fludioxonil [131341-86-1]+TX, Benalaxyl[71626-11-4]+TX, Furalaxyl [57646-30-7]+TX, Metalaxyl [57837-19-1]+TX,R-Metalaxyl [70630-17-0]+TX, Ofurace [58810-48-3]+TX, Oxadixyl[77732-09-3]+TX, Benomyl [17804-35-2]+TX, Carbendazim [10605-21-7]+TX,Debacarb [62732-91-6]+TX, Fuberidazole [3878-19-1]+TX, Thiabendazole[148-79-8]+TX, Chlozolinate [84332-86-5]+TX, Dichlozoline[24201-58-9]+TX, Iprodione [36734-19-7]+TX, Myclozoline [54864-61-8]+TX,Procymidone [32809-16-8]+TX, Vinclozoline [50471-44-8]+TX, Boscalid[188425-85-6]+TX, Carboxin [5234-68-4]+TX, Fenfuram [24691-80-3]+TX,Flutolanil [66332-96-5]+TX, Mepronil [55814-41-0]+TX, Oxycarboxin[5259-88-1]+TX, Penthiopyrad [183675-82-3]+TX, Thifluzamide[130000-40-7]+TX, Guazatine [108173-90-6]+TX, Dodine[2439-10-3][112-65-2] (freie Base)+TX, Iminoctadine [13516-27-3]+TX,Azoxystrobin [131860-33-8]+TX, Dimoxystrobin [149961-52-4]+TX,Enestroburin {Proc. BCPC+TX, Int. Congr.+TX, Glasgow+TX, 2003+TX, 1+TX,93}+TX, Fluoxastrobin [361377-29-9]+TX, Kresoxim-methyl[143390-89-0]+TX, Metominostrobin [133408-50-1]+TX, Trifloxystrobin[141517-21-7]+TX, Orysastrobin [248593-16-0]+TX, Picoxystrobin[117428-22-5]+TX, Pyraclostrobin [175013-18-0]+TX, Ferbam[14484-64-1]+TX, Mancozeb [8018-01-7]+TX, Maneb [12427-38-2]+TX, Metiram[9006-42-2]+TX, Propineb [12071-83-9]+TX, Thiram [137-26-8]+TX, Zineb[12122-67-7]+TX, Ziram [137-30-4]+TX, Captafol [2425-06-1]+TX, Captan[133-06-2]+TX, Dichlofluanid [1085-98-9]+TX, Fluoroimide[41205-21-4]+TX, Folpet [133-07-3]+TX, Tolylfluanid [731-27-1]+TX,Bordeaux Mixture [8011-63-0]+TX, Copperhydroxid [20427-59-2]+TX,Copperoxychlorid [1332-40-7]+TX, Coppersulfat [7758-98-7]+TX, Copperoxid[1317-39-1]+TX, Mancopper [53988-93-5]+TX, Oxine-copper [10380-28-6]+TX,Dinocap [131-72-6]+TX, Nitrothal-isopropyl [10552-74-6]+TX, Edifenphos[17109-49-8]+TX, lprobenphos [26087-47-8]+TX, Isoprothiolane[50512-35-1]+TX, Phosdiphen [36519-00-3]+TX, Pyrazophos [13457-18-6]+TX,Tolclofos-methyl [57018-04-9]+TX, Acibenzolar-5-methyl [135158-54-2]+TX,Anilazine [101-05-3]+TX, Benthiavalicarb [413615-35-7]+TX, Blasticidin-S[2079-00-7]+TX, Chinomethionat [2439-01-2]+TX, Chloroneb [2675-77-6]+TX,Chlorothalonil [1897-45-6]+TX, Cyflufenamid [180409-60-3]+TX, Cymoxanil[57966-95-7]+TX, Dichlone [117-80-6]+TX, Diclocymet [139920-32-4]+TX,Diclomezine [62865-36-5]+TX, Dicloran [99-30-9]+TX, Diethofencarb[87130-20-9]+TX, Dimethomorph [110488-70-5]+TX, SYP-LI90 (Flumorph)[211867-47-9]+TX, Dithianon [3347-22-6]+TX, Ethaboxam [162650-77-3]+TX,Etridiazole[2593-15-9]+TX, Famoxadone [131807-57-3]+TX, Fenamidone[161326-34-7]+TX, Fenoxanil [115852-48-7]+TX, Fentin [668-34-8]+TX,Ferimzone [89269-64-7]+TX, Fluazinam [79622-59-6]+TX, Fluopicolide[239110-15-7]+TX, Flusulfamide [106917-52-6]+TX, Fenhexamid[126833-17-8]+TX, Fosetyl-aluminium [39148-24-8]+TX, Hymexazol[10004-44-1]+TX, lprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid)[120116-88-3]+TX, Kasugamycin [6980-18-3]+TX, Methasulfocarb[66952-49-6]+TX, Metrafenone [220899-03-6]+TX, Pencycuron[66063-05-6]+TX, Phthalide [27355-22-2]+TX, Polyoxins [11113-80-7]+TX,Probenazole [27605-76-1]+TX, Propamocarb [25606-41-1]+TX, Proquinazid[189278-12-4]+TX, Pyroquilon [57369-32-1]+TX, Quinoxyfen[124495-18-7]+TX, Quintozene [82-68-8]+TX, Schwefel [7704-34-9]+TX,Tiadinil [223580-51-6]+TX, Triazoxide [72459-58-6]+TX, Tricyclazole[41814-78-2]+TX, Triforine [26644-46-2]+TX, Validamycin [37248-47-8]+TX,Zoxamide (RH7281) [156052-68-5]+TX, Mandipropamid [374726-62-2]+TX, thecompound of formula F-1

wherein Ra₅ is trifluoromethyl or difluoromethyl (WO2004/058723)+TX,;the compound of formula F-2

wherein Ra₆ is trifluoromethyl or difluoromethyl (WO2004/058723)+TX,;the racemic compound of formula F-3 (syn)

wherein Ra₇ is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, theracemic mixture of formula F-4 (anti)

wherein Ra₇ is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, thecompound of formula F-5

which is an epimeric mixture of racemic compounds of formulae F-3 (syn)and F-4 (anti),wherein the ratio from racemic compounds of formula F-3 (syn) to racemiccmpounds of formula F-4 (anti) is from 1000:1 to 1:1000 and wherein Ra₇is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, the compound offormula F-6

wherein Ra₈ is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, theracemic compound of formula F-7 (trans)

wherein Ra₉ is trifluoromethyl or difluoromethyl (WO03/074491)+TX, theracemic compound of formula F-8 (cis)

wherein Ra₉ is trifluoromethyl or difluoromethyl (WO03/074491)+TX, thecompound of formula F-9

which is a mixture of the racemic compounds of formulae F-7 (trans) andF-8 (cis), wherein the ratio of the racemic compound of formula F-7(trans) to the racemic compound of formula F-8 (cis) is 2:1 to 100:1;and wherein Ra₉ is trifluoromethyl or difluoromethyl (WO03/074491)+TX,the compound of formula F-10

wherein R₁₀ is trifluoromethyl or difluoromethyl (WO2004/058723)+TX, theracemic compound of formula F-11 (trans)

wherein R₁₁ is trifluoromethyl or difluoromethyl (WO03/074491)+TX, theracemic compound of formula F-12 (cis)

wherein R₁₁ is trifluoromethyl or difluoromethyl (WO03/074491)+TX, thecompound of formula F-13

which is a racemic mixture of formulae F-11 (trans) and F-12 (cis), andwherein R₁₁ is trifluoromethyl or difluoromethyl (WO 03/074491)+TX, andthe compound of formula F-14

(WO2004/058723)+TX, and the compound of formula F-15

The references in brackets behind the active ingredients, e.g.[3878-19-1] refer to the Chemical Abstracts Registry number. Thecompounds of formulae A-1 to A-26 are described in WO 03/015518 or in WO04/067528. The above described mixing partners are known. Where theactive ingredients are included in “The Pesticide Manual” [The PesticideManual—A World Compendium; Thirteenth Edition; Editor: C. D. S. Tomlin;The British Crop Protection Council], they are described therein underthe entry number given in round brackets hereinabove for the particularcompound; for example, the compound “abamectin” is described under entrynumber (1). Where “[CCN]” is added hereinabove to the particularcompound, the compound in question is included in the “Compendium ofPesticide Common Names”, which is accessible on the internet [A. Wood;Compendium of Pesticide Common Names, Copyright© 1995-2004]; forexample, the compound “acetoprole” is described under the internetaddress http://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred tohereinabove by a so-called “common name”, the relevant “ISO common name”or another “common name” being used in individual cases. If thedesignation is not a “common name”, the nature of the designation usedinstead is given in round brackets for the particular compound; in thatcase, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemicalname”, a “traditional name”, a “compound name” or a “development code”is used or, if neither one of those designations nor a “common name” isused, an “alternative name” is employed. “CAS Reg. No” means theChemical Abstracts Registry Number.

The mixtures comprising a compound of formula I and one or more activeingredients as described above can be applied, for example in a single“ready-mix” form, in a combined spray mixture composed from separateformulations of the single active ingredient components, such as a“tank-mix”, and also in a combined use of the single active ingredientswhen applied in a sequential manner, i.e. one after the other with areasonably short period, such as a few hours or days. The order ofapplying the components (I) and active ingredients as described above isnot essential for working the present invention.

BIOLOGICAL EXAMPLES %=Percent by Weight, Unless Otherwise SpecifiedExample B1 Activity Against Aphis craccivora

Pea seedlings are infected with Aphis craccivora, subsequently sprayedwith a spray mixture comprising 400 ppm of active ingredient and thenincubated at 20°. 3 and 6 days later, the percentage reduction in thepopulation (% activity) is determined by comparing the number of deadaphids between the treated and untreated plants. In this test, compoundslisted in the Tables above show good activity.

Example B2 Activity Against Diabrotica balteata

Maize seedlings are sprayed with an aqueous emulsion spray mixturecomprising 400 ppm of active ingredient and, after the spray coating hasdried on, populated with 10 larvae (2nd instar) of Diabrotica balteataand introduced into a plastic container. 6 days later, the percentagereduction in the population (% activity) is determined by comparing thenumber of dead larvae between the treated and untreated plants.

In this test, compounds listed in the Tables above show good activity.In particular compounds P1, P2, P6, P7, P24, P29, P25, P60, P62, P63,P48, P46, P50, P23, P8, P66, P22, P14, P21, P11, P67, P68 have anactivity of over 80%.

Example B3 Activity Against Heliothis virescens Foliar Application

Young soya plants are sprayed with an aqueous emulsion spray mixturecomprising 400 ppm of active ingredient and, after the spray coating hasdried on, populated with 10 caterpillars (1st instar) of Heliothisvirescens and introduced into a plastic container. 6 days later, thepercentage reduction in the population and in the feeding damage (%activity) are determined by comparing the number of dead caterpillarsand the feeding damage between the treated and untreated plants.

In this test, compounds listed in the Tables above show good activity.In particular compounds P1, P2, P6, P10, P3, P7, P15, P24, P51, P50,P63, P62, P61, P60, P12, P65, P66, P9, P8, P67, P68, P23, P21, P10, P11,P47, P52, P53 have an activity of over 80%.

Example B4 Activity Against Heliothis virescens Application to Eggs

Heliothis virescens eggs, which have been deposited on cotton, aresprayed with an aqueous emulsion spray mixture comprising 400 ppm ofactive ingredient. After 8 days, the percentage hatching rate of theeggs and the survival rate of the caterpillars (% activity) areevaluated in comparison with untreated control batches.

In this test, compounds listed in the Tables above show good activity.In particular compound P1, P2, P6, P7, P39, P3, P10, P24, P46, P48, P50,P51, P29, P31, P25, P67, P63, P62, P61, P60, P64, P68, P10, P8, P32, P9,P30, P23, P14, P21, P11, P40, P69, P70, P71, P72 have an activity ofover 80%.

Example B5 Activity Against Myzus persicae Foliar Application

Pea seedlings are infected with Myzus persicae, subsequently sprayedwith a spray mixture comprising 400 ppm of active ingredient and thenincubated at 20°. 3 and 6 days later, the percentage reduction in thepopulation (% activity) is determined by comparing the number of deadaphids between the treated and untreated plants.

In this test, compounds listed in the Tables above show good activity.

Example B6 Activity Against Myzus Persicae Systemic Application

Pea seedlings are infected with Myzus persicae, and their roots aresubsequently placed into a spray mixture comprising 400 ppm of activeingredient. The seedlings are then incubated at 20°. 3 and 6 days later,the percentage reduction in the population (% activity) is determined bycomparing the number of dead aphids between the treated and untreatedplants.

In this test, compounds listed in the Tables above show good activity.

Example B7 Activity Against Plutella xylostella

Young cabbage plants are sprayed with an aqueous emulsion spray mixturecomprising 400 ppm of active ingredient and, after the spray coating hasdried on, populated with 10 caterpillars (3rd instar) of Plutellaxylostella and introduced into a plastic container. 3 days later, thepercentage reduction in the population and in the feeding damage (%activity) are determined by comparing the number of dead caterpillarsand the feeding damage between the treated and untreated plants.

In this test, compounds listed in the Tables above show good activity.In particular compounds P1, P2, P6, P39, P3, P41, P7, P10, P15, P24,P29, P31, P25, P8, P9, P32, P30, P12, P13, P23, P22, P63, P62, P61, P60,P64, P63, P14, P46, P48, P50, P51, P17, P65, P66, P21, P18, P10, P67,P68, P16, P11, P35, P52, P53, P38, P40, P70 have an activity of over80%.

Example B8 Activity Against Spodoptera littoralis

Young soya plants are sprayed with an aqueous emulsion spray mixturecomprising 400 ppm of active ingredient and, after the spray coating hasdried on, populated with 10 caterpillars (1st instar) of Spodopteralittoralis and introduced into a plastic container. 3 days later, thepercentage reduction in the population and in the feeding damage (%activity) are determined by comparing the number of dead caterpillarsand the feeding damage between the treated and untreated plants.

In this test, compounds listed in the Tables above show good activity.In particular compounds P1, P2, P3, P6, P39, P41, P10, P63, P62, P61,P60, P64, P24, P7, P10, P67, P68, P29, P31, P25, P8, P32, P30, P9, P23,P14, P65, P66, P21, P11, P35, P34, P33, P38, P40, P69, P52, P53, P70have an activity of over 80%.

Example B9 Activity Against Cydia

Standard Cydia diet cubes (1.5 cm width) are pierced with a tooth-pickand are immersed in liquid paraffin (ca. 80° C.). After the paraffincoat has hardened, an aqueous emulsion containing 400 ppm of activeingredient is applied using a De Vilbis sprayer (25 ml, 1 bar). Afterthe spray coating has dried, the cubes are put into plastic containerswhich are then populated with two freshly hatched Cydia pomonella(1^(st) instar). The containers are then closed with a plastic cap.After 14 days incubation at 26° C. and 40-60% relative humidity, thesurvival rate of the caterpillars as well as their growth regulation isdetermined. In this test, compounds listed in the Tables above show goodactivity. In particular compounds P22, P6, P11, P65, P66, P17, P63, P62,P61, P60, P2, P3, P14, P67, P68, P15, P7, P21, P10, P24, P8, P13, P9,P23, P12 have an activity of over 80%.

Example B10 Comparison of the Insecticidal Activity of CompoundsAccording to the Invention with the Structurally Most Closely ComparableCompound from the State of the Art (Compound No. 566 Described on Page122 of WO03/024222)

(Compound No. P41 according to this invention)

(Cpd No. 566 According to the State of the Art)B10a: Systemic Insecticide Test for Spodoptera littoralis (CottonLeafworm):

Four day old maize seedlings (Zea mais, variety Stoneville) are placedindividual in vials containing 24 ml water into which the chemical isdiluted at the prescribed concentrations (12.5, 3 and 0.8 ppm).Seedlings are allowed to grow for six days. Subsequently leaves are cutand placed in a Petri dish (5 cm diameter), inoculated with twelve tofifteen 1st instar S. littoralis larvae and incubated for four days in agrowth chamber (25° C., 50% r.h., 18:6 L:D photo period). Number ofalive insects are counted and percentage of dead calculated. Tests wereconducted with one replicate. Results are shown in Table B10a:

TABLE B10a Systemic Insecticide Test for Spodoptera littoralis Deathrate (%) after 4 Compound: Concentration (ppm) days Comp. 566 (state ofthe art) 3 0 Comp. 566 (state of the art) 0.8 0 Comp. 566 (state of theart) 0.2 0 Comp. P41 (invention) 3 100 Comp. P41 (invention) 0.8 80Comp. P41 (invention) 0.2 20

Table B10a shows that compound No. P41 according to the invention exertsa substantially better insecticidal action on Spodoptera littoralis thanthe compound from the state of the art. Especially at low applicationrates (3 and 0.8 ppm) the compound according to the invention is farsuperior to the compound of the state of the art. This enhanced effectwas not to be expected on the basis of the structural similarity ofthese compounds.

B10b: Insecticide Test for Heliothis virescens (Tobacco Budworm):

50-60 newly laid H. virescens eggs were placed on artificial diet inPetri dishes (5 cm diameter) and topically treated with 0.8 ml solutionof compounds at the following rates: 3, 0.8, 0.2, 0.05. Petri dishes aremaintained at 26±2° C., 50±10% r.h. in a dark room and assessmentconducted one week after application (two replicates/treatment). Larvaemortality and effects on larvae growth were compared to the control.Results are shown in Table B10b:

TABLE B10 b Insecticide Test for Heliothis virescens Percent larvaeshowing growth Percent reduction Concentration larvae (comparedCompound: (ppm) mortality to control) Comp. 566 (state 3 0 0 of the art)Comp. 566 (state 0.8 0 0 of the art) Comp. 566 (state 0.2 0 0 of theart) Comp. 566 (state 0.05 0 0 of the art) Comp. P41 (invention) 3 0 100Comp. P41 (invention) 0.8 0 100 Comp. P41 (invention) 0.2 0 45 Comp. P41(invention) 0.05 0 0

Table B10b shows that compound No. P41 according to the invention exertsa substantially better insecticidal action on Heliothis virescens thanthe compound from the state of the art. Especially at low applicationrates (3, 0.8 and 0.2 ppm) the compound according to the invention isfar superior to the compound of the state of the art. This enhancedeffect was not to be expected on the basis of the structural similarityof these compounds.

B10 c: Insecticide Test for Plutella xylostella (Diamond Back Moth):

Chinese cabbage plants were sprayed with insecticide at 3, 0.8, 0.2 and0.05 ppm. Five cm diameter leaf disks were cut and placed in a Petridish containing 6 ml agar (0.8%). Five P. xylostella larvae L3 wereintroduced into Petri dishes and kept at 26±2° C., 50±10% r.h. in a darkroom (two replicates per treatment). Number of alive insects werecounted and percentage of dead calculated after three days. Results areshown in Table B10c:

TABLE B10 c Insecticide Test for Plutella xylostella Death rate (%)after 5 Compound: Concentration (ppm) days Comp. 566 (state of the art)3 25 Comp. 566 (state of the art) 0.8 5 Comp. 566 (state of the art) 0.210 Comp. 566 (state of the art) 0.05 0 Comp. P41 (invention) 3 60 Comp.P41 (invention) 0.8 80 Comp. P41 (invention) 0.2 0 Comp. P41 (invention)0.05 0Table B10c shows that compound No. P41 according to the invention exertsa substantially better insecticidal action on Plutella xylostella thanthe compound from the state of the art. Especially at low applicationrates (3 and 0.8 ppm) the compound according to the invention is farsuperior to the compound of the state of the art. This enhanced effectwas not to be expected on the basis of the structural similarity ofthese compounds.

1. A compound of formula I

and agrochemically acceptable salts, enantiomers, tautomers, andN-oxides thereof, wherein each of E and Z, which may be the same ordifferent, represents oxygen or sulfur; A is a bivalent three- toten-membered monocyclic or fused bicyclic ring system which can bepartially saturated or fully saturated and can contain 1to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur,wherein each ring system does not contain more than 2 oxygen atoms andmore than 2 sulfur atoms; and wherein the three- to ten-membered ringsystem may be mono-, di- or trisubstituted by halogen, cyano, nitro,hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl,C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl,C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C ₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C-C₄haloalkoxy, C₁-C₄alkylthio,C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl,C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy,C₃-C₆dialkylaminocarbonyloxy, C₃-C₆trialkylsilyl, or by a three- toten-membered monocyclic or fused bicyclic ring system which can bearomatic, partially saturated or fully saturated and can contain 1to 4hetero atoms selected from the group consisting of nitrogen, oxygen andsulfur, wherein each ring system does not contain more than 2 oxygenatoms and more than 2 sulfur atoms, and wherein the three- toten-membered ring system itself may be mono-, di- or trisubstituted byhalogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl,C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl,C₅-C₇halocycloalkenyl, C₅-C ₈halocycloalkynyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino,C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino,C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy,C₃-C₆trialkylsilyl or phenyl, it being possible for the phenyl group inturn to be substituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio,C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio,cyano-C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C ₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C ₆haloalkylsulfonyl, aminosulfonyl,C₁-C₂alkylaminosulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl,di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents atnitrogen atoms in the ring systems being other than halogen; X isoxygen, NH or C₁-C₄alkyl-N; Y is C₁-C₆alkylene, C₂-C₆alkenylene,C₂-C₆alkynylene, or a bivalent three- to ten-membered monocyclic orfused bicyclic ring system which can be partially saturated or fullysaturated and can contain 1to 4 hetero atoms selected from the groupconsisting of nitrogen, oxygen and sulfur, wherein each ring system doesnot contain more than 2 oxygen atoms and more than 2 sulfur atoms; andwherein the three- to ten-membered ring system and the C₁-C₆alkylene,C₂-C₆alkenylene and C₂-C₆alkynylene groups may be mono-, di- ortrisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl,C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,C₃- C₆halocycloalkyl, C₅-C ₇halocycloalkenyl, C₅-C ₈halocycloalkynyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,C₁-C₄alkylsulfinyl, C₁-C ₄alkylsulfonyl, C₁-C₄alkylamino,C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl,C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy,C₃-C₆dialkylaminocarbonyloxy, C₃-C₆trialkylsilyl, or by a three- toten-membered monocyclic or fused bicyclic ring system which can bearomatic, partially saturated or fully saturated and can contain 1to 4hetero atoms selected from the group consisting of nitrogen, oxygen andsulfur, wherein each ring system does not contain more than 2 oxygenatoms and more than 2 sulfur atoms, and wherein the three- toten-membered ring system itself may be mono-, di- or trisubstituted byhalogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl,C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl,C₅-C₇halocycloalkenyl, C₅-C ₈halocycloalkynyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino,C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino,C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy,C₃-C₆trialkylsilyl or phenyl, wherein the phenyl group may besubstituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C ₆haloalkenylthio,C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio,cyano-C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆halo-alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl,C₁-C₂alkylamino-sulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl,di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents atnitrogen atoms in the ring systems being other than halogen; p is 0 or1; q is 0 or 1; B is a three- to four-membered ring system which isfully or partially saturated and can contain a hetero atom selected fromthe group consisting of nitrogen, oxygen and sulfur, and wherein thethree- to four-membered ring system itself may be mono-, di- ortrisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl,C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,C₁-C₄alkylsulfinyl, C₁-C ₄alkylsulfonyl, C₁-C₄alkylamino,C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl,C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy,C₃-C₆dialkylaminocarbonyloxy, C₃-C₆trialkylsilyl, or by a three- toten-membered monocyclic or fused bicyclic ring system which can bearomatic, partially saturated or fully saturated and can contain 1to 4hetero atoms selected from the group consisting of nitrogen, oxygen andsulfur, wherein each ring system does not contain more than 2 oxygenatoms and more than 2 sulfur atoms, and wherein the three- toten-membered ring system itself may be mono-, di- or trisubstituted byhalogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl,C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl,C₅-C₇halocycloalkenyl, C₅-C ₈halocycloalkynyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino,C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino,C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy,C₃-C₆trialkylsilyl or phenyl, wherein the phenyl group in turn may besubstituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkylthio,C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆halo-alkenylthio,C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C ₄alkoxycarbonyl-C₁-C₃alkylthio,cyano-C₁-C₃alkylthio, C₁-C ₆alkylsulfinyl, C₁-C₆halo-alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl,C₁-C₂alkylamino-sulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl,di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents atnitrogen atoms in the ring systems being other than halogen; each R₁independently is halogen, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl,C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl,C₁-C₄haloalkylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl,C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy,C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl, phenyl, benzyl orphenoxy, or phenyl, benzyl or phenoxy mono-, di- or trisubstituted byhalogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio,C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl,C₂-C₆alkoxycarbonyloxy, C₂-C₆alkyl aminocarbonyloxy,C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl; or each R₁independently is amino, formyl, C₂-C₆cyanoalkenyl,C₂-C₆alkylcarbonylamino, phenylcarbonylamino which can be mono-, di- ortrisubstituted by halogen, cyano, nitro, halogen, C₁-C₆alkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino,C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino,C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy orC₃-C₆-trialkylsilyl; or each R₁ independently is 2-,3- or4-pyridylcarbonylamino which can be mono-, di- or trisubstituted byhalogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio,C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl,C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy,C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl; or each R₁independently is C₂-C₆alkoxycarbonylamino, C₂-C₆alkylaminocarbonylamino,C₃-C₆dialkylaminocarbonylamino, C₂-C₆haloalkylcarbonyl or is a groupR_(x)ON═C(R_(y))—, wherein R_(x) and R_(y) independently are hydrogen orC₁-C₆alkyl; n is 0, 1, 2, 3 or 4; each of R₂ and R₃, which may be thesame or different, represents hydrogen, C₁-C₆alkyl, C₂-C₆alkenyl,C₂-C₆alkynyl or C₃-C₈cycloalkyl; or C₁-C₆alkyl, C₂-C₆alkenyl,C₂-C₆alkynyl or C₃-C₈cycloalkyl substituted by one or more substituentsselected from halogen nitro, cyano, hydroxy, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino,C₃-C₆cycloalkylamino or C₁-C₆alkyl-C₃-C₆cycloalkylamino; D is phenyl,2-pyridyl, 3-pyridyl or 4-pyridyl; or phenyl, 2-pyridyl, 3-pyridyl or4-pyridyl mono-, di- or trisubstituted by C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, halogen, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl or C₁-C₄haloalkylsulfonyl; orD is a group

R₄, R₄′, R₁₀, R₁₇, and R₁₉ independently from each other, are hydrogen,C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, halogen, cyano,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₄alkoxycarbonyl, C₁-C₄alkylthio,C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄haloalkylsulfinyl or C₁-C₄haloalkylsulfonyl; R₅, R₆, R₈, R₁₁, R₁₂,R₁₅, R₁₆ and R₁₈ independently from each other, are C₁-C₆alkyl orC₁-C₆alkyl mono-, di- or trisubstituted by halogen, cyano, nitro,hydroxy, C₁-C₄alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino,C₂-C₄dialkylamino or C₃-C₆cycloalkylamino; or are phenyl, 2-pyridyl,3-pyridyl, 4-pyridyl; or are phenyl, 2-pyridyl, 3-pyridyl or 4-pyridylmono-, di- or trisubstituted by C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, halogen, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl or C₁-C₄haloalkylsulfonyl;and R₇, R₉, R₁₃ and R₁₄ independently from each other, are hydrogen,C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₃-C₆alkenylor C₃-C₆haloalkenyl.
 2. A compound according to claim 1, wherein R₄′ ishydrogen and each R₁ independently is halogen, nitro, hydroxy,C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino,C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino,C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy orC₃-C₆-trialkylsilyl, phenyl, benzyl or phenoxy, or phenyl, benzyl orphenoxy mono-, di- or trisubstituted by halogen, cyano, nitro, halogen,C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino,C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino,C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy orC₃-C₆-trialkylsilyl.
 3. A compound according to claim 1, wherein B is athree- to four-membered ring system which is fully or partiallysaturated, and wherein the three- to four-membered ring system itselfmay be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy,C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl,C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl,C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl,C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio,C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino,C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl,C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy,C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl, or by a three- toten-membered monocyclic or fused bicyclic ring system which can bearomatic, partially saturated or fully saturated and can contain 1 to 4hetero atoms selected from the group consisting of nitrogen, oxygen andsulfur, wherein each ring system does not contain more than 2 oxygenatoms and more than 2 sulfur atoms, and wherein the three-toten-membered ring system itself to be mono-, di- or trisubstituted byhalogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl,C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl,C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl,C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino,C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino,C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl,C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy,C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy,C₃-C₆-trialkylsilyl or phenyl, wherein the phenyl group in turn may besubstituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio,C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio,C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio,C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio,cyano-C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl,C₁-C₂alkylaminosulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl,di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents atnitrogen atoms in the ring systems being other than halogen.
 4. Acompound according to claim 1, wherein A is C₃-C₆cycloalkylene.
 5. Acompound according to claim 1, wherein B is cyclopropyl or cyclobutylwhich may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl,hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio.
 6. A compound accordingto claim 1, wherein D is the group D₁.
 7. A pesticidal composition,which comprises at least one compound according to claim 1 or, whereappropriate, a tautomer thereof, in each case in free form or inagrochemically utilizable salt form, as active ingredient and at leastone auxiliary.
 8. A composition according to claim 7 for controllinginsects or representatives of the order Acarina.
 9. A method forcontrolling pests, which comprises applying a composition according toclaim 7 to the pests or their environment.
 10. A method according toclaim 9 for controlling insects or representatives of the order Acarina.11. A method according to claim 9 for the protection of plantpropagation material from the attack by pests, which comprises treatingthe propagation material or a site where the plant propagation materialis planted.
 12. Plant propagation material treated in accordance withthe method described in claim
 11. 13. A process for the preparation of acompound of formula I according to claim 1 or, where appropriate, atautomer thereof, in each case in free form or in salt form, whichcomprises a) for the preparation of a compound of formula I, in which R₂is hydrogen and E and Z are oxygen, or, where appropriate, a tautomer orsalt thereof, reacting a compound of formula II

in which R₁, n, and D have the meanings given for formula I in claim 1,or, where appropriate, a tautomer or salt thereof with a compound offormula IIIHN(R₃)-A-(X)_(p)—(Y)_(q)—B  (III), in which R₃, A, X, Y, p, q and B havethe meanings given for formula I, or, where appropriate, with a tautomerand/or salt thereof or, b) for the preparation of a compound of formulaI, or, where appropriate, a tautomer and/or salt thereof, reacting acompound of formula IV

in which R₁, R₂, n, Z and D have the meanings given for the formula I inclaim 1; and X₁ is a leaving group, or, where appropriate, a tautomerand/or salt thereof with a compound of formula IIIHN(R₃)-A-(X)_(p)—(Y)_(q)—B  (III), in which R₃, A, X, Y, p, q and B havethe meanings given for formula I, or, where appropriate, with a tautomersalt thereof or, c) for the preparation of a compound of formula I, or,where appropriate, a tautomer and/or salt thereof, reacting a compoundof formula V

in which R₁, R₂, R₃, n, A, X, Y, Z and B have the meanings given for theformula I in claim 1, or, where appropriate, a tautomer or salt thereofwith a compound of formula VIX₂C(═O)D  (VI), in which D has the meaning given for formula I in claim1; and X₂ is a leaving group, or, where appropriate, with a tautomersalt thereof.
 14. A compound according to claim 1, wherein A and B areeach independently cyclopropyl, and p=q=0.
 15. A compound according toclaim 14, wherein n=2, a first R₁ is a methyl group and a second R₁ is achloro group.
 16. A compound according to claim 15, wherein D is thegroup D₁.
 17. A compound according to claim 16, wherein R₄ is atrifluoromethyl group, R_(4′) is hydrogen, R₅ is a 3-chloro-2-pyridylgroup, each of E and Z represents oxygen, and each of R₂ and R₃represents hydrogen.
 18. A pesticidal composition, which comprises atleast one compound according to claim 4 or, where appropriate, atautomer thereof, in each case in free form or in agrochemicallyutilizable salt form, as active ingredient and at least one auxiliary.19. A pesticidal composition, which comprises at least one compoundaccording to claim 14 or, where appropriate, a tautomer thereof, in eachcase in free form or in agrochemically utilizable salt form, as activeingredient and at least one auxiliary.
 20. A method for controllingpests, which comprises applying a composition according to claim 19 tothe pests or their environment.